Herbicidal sulfonamides

ABSTRACT

Hydroxymethylbenzenesulfonamide derivatives have utility as agricultural chemicals and in particular as herbicides.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a continuation-in-part of my copending applicationSer. No. 168,352, filed July 11, 1980, now abandoned.

BACKGROUND OF THE INVENTION

This invention relates to hydroxymethylbenzenesulfonamide derivativeswhich are useful as agricultural chemicals and in particular as generalherbicides having both pre- and post-emergence activity.

Netherlands Pat. No. 121,788, published Sept. 15, 1966, discloses thepreparation of compounds of the following Formula and their use asgeneral or selective herbicides: ##STR1## wherein R₁ and R₂ mayindependently be alkyl of 1-4 carbon atoms; and

R₃ and R₄ may independently be hydrogen, chlorine or alkyl of 1-4 carbonatoms.

U.S. Pat. No. 3,637,366 discloses compounds having the formula: ##STR2##wherein R₁ is hydrogen or lower saturated aliphatic acyl and

R₂ is hydrogen, 2-pyrimidinyl, pyridyl, amidino, acetyl or carbamoyl.

The disclosed compounds are said to provide control of crabgrass, cress,endive, clover and Poa annua.

French Pat. No. 1,468,747 discloses the following para-substitutedphenylsulfonamides as being useful as antidiabetic agents: ##STR3##wherein R═H, halogen, CF₃ or alkyl.

Logemann et al. Chem Ab., 53, 18052 g (1969), disclose a number ofsulfonamides, including uracil derivatives and those having the formula:##STR4## wherein R is butyl, phenyl, or ##STR5## and R₁ is hydrogen ormethyl.

When tested for hypoglycemic effect in rats (oral doses of 25 mg/100 g),the compounds in which R is butyl and phenyl were most potent. Theothers were of low potency or inactive.

Wojciechowski, J. Acta. Polon. Pharm 19, p. 121-5 (1962) [Chem. Ab., 591633 e] describes the synthesis ofN-[(2,6-dimethoxypyrimidin-4-yl)aminocarbonyl]-4-methylbenzenesulfonamide:##STR6## Based upon similarity to a known compound, the authorspeculated that the foregoing compound might have a hypoglycemicactivity.

Substituted-pyrimidinyl sulfonylureas of the following formula, whichare also para-substituted on the phenyl ring, are disclosed in FarmcoEd. Sci., 12, 586 (1957) [Chem. Ab., 53, 18052 g (1959]: ##STR7##wherein R═H or CH₃.

The presence of undesired vegetation causes substantial damage to usefulcrops, especially agricultural products that satisfy man's basic foodand fiber needs, such as cotton, rice, corn, wheat, and the like. Thecurrent population explosion and concomitant world food and fibershortage demand improvements in the efficiency of producing these crops.Preventing or minimizing loss of a portion of such valuable crops bykilling, or inhibiting the growth of undesired vegetation is one way ofimproving this efficiency. A wide variety of materials useful forkilling or inhibiting (controlling) the growth of undesired vegetationis available; such materials are commonly referred to as herbicides. Theneed still exists however, for more effective herbicides.

SUMMARY OF THE INVENTION

This invention relates to novel compounds of Formula I and theiragriculturally suitable salts, suitable agricultural compositionscontaining them, and their method of use as general and selectivepreemergence and post-emergence herbicides and as plantgrowth regulants.##STR8## wherein L is OH, OC(O)R₁₁, OC(O)NHR₁₂ or OC(O)OR₁₃ ;

R is H, F, Cl, Br, NO₂, CF₃, C₁ -C₃ alkyl or C₁ -C₃ alkoxy;

R₁ is H or C₁ -C₄ alkyl;

R₂ is H or CH₃ ;

R₈ is H, CH₃ or OCH₃ ;

R₁₁ is H, C₁ -C₅ alkyl, C₂ -C₃ alkenyl, C₂ -C₃ alkynyl, C₃ -C₄cycloalkyl, ##STR9## C₁ -C₄ alkyl substituted with 1-4 substituentsselected from 0-3 F., 0-3 Cl or 0-3 Br, or C₂ -C₃ alkenyl substitutedwith 1-3 Cl;

R₁₂ is H, C₁ -C₆ alkyl, C₃ -C₄ alkenyl, C₅ -C₆ cycloalkyl, ##STR10## C₅-C₆ cycloalkyl substituted with CH₃ ; R₁₃ is C₁ -C₆ alkyl or ##STR11##R₁₄ and R₁₅ are independently H, NO₂, CH₃, Cl or OCH₃ ;

R₁₆ is H, F, Cl, Br, C₁ -C₃ alkyl, NO₂, CN, SO₂ CH₃, OCH₃, SCH₃ or CF₃ ;

R₁₇ H, Cl or C₁ -C₃ alkyl;

R₁₈ is H, CH₃ or Cl;

A is ##STR12## W is O or S; X is H, Cl, Br, CH₃, CH₂ CH₃, C₁ -C₃ alkoxy,CF₃, SCH₃ or CH₂ OCH₃ ;

Y is CH₃ or OCH₃ ;

Z is N, CH, CCl, CBr, CCN, CCH₃, CCH₂ CH₃, CCH₂ CH₂ Cl or CCH₂ CH═CH₂ ;

Y¹ is H, CH₃, OCH₃ or OCH₂ CH₃ ; and

Q is O or CH₂ ;

and their agriculturally suitable salts; provided that when W is S, thenR₈ is H.

Preferred Compounds

Preferred for their higher activity and/or more favorable ease ofsytnthesis are:

(1) Compounds of the generic scope where Z is N, CH, CCl, CBr or CCH₃, Wis O and R₈ is H or CH₃.

(2) Compounds of the generic scope where L is OH, R is H, R₁ and R₂ areCH₃, R₈ is H or CH₃ ; A is ##STR13## Z is CH or N; X and Y areindependently CH₃ or OCH₃ ; and W is O;

(3) Compounds of Preferred (1) where Z is CH or N; X is CH₃ or OCH₃ ;and R₁ is H or CH₃ ;

(4) Compounds of Preferred (3) where R and R₈ are H, and A is ##STR14##(5) Compounds of Preferred (4) where R₁₁, R₁₂ and R₁₃ are C₁ -C₃ alkyl;

(6) Compounds of Preferred (4) where L is OH.

Specifically preferred for their highest activity and/or most favorableease of synthesis are:

N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(hydroxymethyl)benzenesulfonamide,mp 149°-151°;

N-[(4,6-Dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-(hydroxymethyl)benzenesulfonamide,mp 146°-148° (d);

N-[(4,6-Dimethylpyrimidin-2-yl)aminocarbonyl]-2-(hydroxymethyl)benzenesulfonamide;

N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-(hydroxymethyl)benzenesulfonamide;

N-[(4,6-Dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-(hydroxymethyl)benzenesulfonamide;and

N-[(4-Methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-(hydroxymethyl)benzenesulfonamide.

DETAILED DESCRIPTION OF THE INVENTION Synthesis

Many of the compounds of Formula I may be prepared as shown in Equation1 by reaction of an appropriately substitutedo-hydroxymethylbenzenesulfonylurea, II, with an appropriate acidchloride. ##STR15##

The reaction of Equation 1 is best carried out in inert aprotic solventssuch as methylene chloride, tetrahydrofuran or acetonitrile at 0°-80° C.An excess of the acid chloride is used and at least one equivalent of atertiary amine such as pyridine, triethylamine or4-dimethylaminopyridine. Isolation is achieved by evaporation of solventand recrystallization from suitable solvents such as 1-chlorobutane,ethyl acetate or ethyl ether or by column chromatography over silicagel.

Other compounds of Formula I may be prepared as shown in Equation 2 byreaction of an appropriately substitutedo-hydroxymethylbenzenesulfonylurea, II, with an appropriate isocyanate.##STR16##

The reaction of Equation 2 is best carried out in inert aprotic solventssuch as methylene chloride, tetrahydrofuran or acetonitrile at 0°-80° C.An excess of the isocyanate is used and a catalyst such asdibutyltindilaurate or 1,4-diaza[2,2,2]bicyclooctane (DABCO). Isolationis achieved by evaporation of solvent and recrystallization fromsuitable solvents such as 1-chlorobutane, ethyl acetate or ethyl etheror by column chromatography over silica gel.

Other compounds of Formula I may be prepared as shown in Equation 3 byreaction of an appropriately substitutedo-hydroxymethylbenzenesulfonylurea, II, with an appropriatechloroformate. ##STR17##

The reaction of Equation 3 is best carried out in inert aprotic solventssuch as methylene chloride, tetrahydrofuran or acetonitrile at 0°-80° C.An excess of the chlorocarbonate is used and at least one equivalent ofa tertiary amine such as pyridine, triethylamine or4-dimethylaminopyridine. Isolation is achieved by evaporation of solventand recrystallization from suitable solvents such as 1-chlorobutane,ethyl acetate or diethyl ether or by column chromatography over silicagel.

The preparation of compounds of Formula II where R₁ ═R₂ ═H may beprepared as shown in Equation 4. ##STR18##

The carboxylic acid, VI, may be converted to the alcohol by reductionwith 4-5 equivalents of borane-THF reagent in THF at ambient pressureand temperature for 4 to 18 hours. Isolation is achieved by drowning indilute acid followed by extraction of the product with a solvent such asmethylene chloride, ethyl acetate or ethyl ether. Evaporation of solventand crystallization of column chromatography on silica gel affords thepure alcohol, VII.

The carboxylic acids, VI, may be prepared by hydrolysis of thecorresponding methyl esters as shown in Equation 5. ##STR19##

When A is a pyrimidine type structure, the methyl esters are besthydrolyzed by dissolving in a solution of 80 parts ethanol, 10 partswater and 10 parts potassium hydroxide. The mixture is stirred atambient temperature for 18 hours followed by pouring into a large excessof water and acidifying to a pH of 2.0. The pure acid, VI, precipitatesand is filtered and washed with water.

When A is a triazine and X or Y is alkoxy, the hydrolysis is bestperformed by dissolving the ester in a solution of potassium t-butoxidein dimethyl sulfoxide at ambient temperature for two hours. Addition ofa large volume of water followed by acidification to a pH of 2.0precipitates the acid, VI.

The preparation of esters of Formula VIII is described in EuropeanPatent Application 7687.

Compounds of Formula VII may also be prepared by treatment of thecarboxylic acids, VI, or the methyl esters, VIII, with lithium aluminumhydride by the procedures described by R. F. Nystrom and W. G. Brown, J.Am. Chem. Soc. 69, 2548 (1947) and R. B. Moffett, Organic Synthesis,Coll. Vol. 4, 834 (1963). Reduction of the esters with sodiumbis(2-methoxyethoxy)aluminum hydride is described in M. Fieser and L. E.Fieser, Reagents for Organic Synthesis, John Wiley & Sons, New York,Vol. 5, p. 596 (1975).

The preparation of compounds of Formula II where R₁ ═H and R₂ ═CH₃ maybe carried out as shown in Equation 6. ##STR20##

Compounds of Formula IX are treated with one equivalent of lithiumaluminum hydride (LAH) in a solvent such as ether, tetrahydrofuran orglyme at -20° to 25° C. for 1 to 6 hours. Next there is a successivedropwise addition of an equivalent number of ml of water as grams of LAHfollowed by an equal number of ml of 15% sodium hydroxide followed by 3times that number of ml of water. This produces a dry granularprecipitate of aluminum oxide which is easy to filter. The aqueous phaseis then acidified with dilute acid and the product extracted withsolvent such as methylene chloride, ethyl acetate or ethyl ether.Evaporation of solvent and crystallization or column chromatography onsilica gel affords the pure alcohol, X.

Compounds of Formula IX are prepared by the reaction, as shown inEquation 7, using an excess of methyl lithium with a carboxylic acidderivative of Formula VI. ##STR21##

Compounds of Formula VI are restricted to structures in which thesubstituents R, Z, X and Y contain no displaceable halogens, NO₂ or CN.

An excess of methyl lithium in a suitable solvent such as diethyl ether,hexane, pentane or benzene is added to a solution or slurry of VI in asimilar solvent at temperatures between -100° and 0° C. The mixture isallowed to warm to room temperature and stir for 30 minutes. Aqueousacid is then added and the compound IX is extracted into a suitablesolvent to free it from salts, followed by evaporation of the solvent.Purification is by chromatography on silica gel.

Another procedure for the preparation of compounds of Formula X is thereaction of excess methyl lithium with the corresponding aldehyde XI asshown in Equation 8. ##STR22##

Compounds of Formula XI are restricted to structures in which thesubstituents R, Z, X and Y contain no displaceable halogens; NO₂ or CN.

An excess of methyl lithium in a suitable solvent such as diethyl ether,hexane, pentane or benzene is added to a solution or slurry of XI in asimilar solvent at temperatures between -100° and 0° C. The mixture isallowed to warm to room temperature and stir for 30 minutes. Aqueousacid is then added and the compound X is extracted into a suitablesolvent to free it from salts followed by evaporation of the solvent.Purification is by chromatography on silica gel.

Aldehydes of Formula XI are prepared by the procedure of Equation 9.##STR23##

Following the procedure of R. Kanayawa and T. Tokoroyama, a solution ofsodium bis(2-methoxyethoxy)aluminum hydride in THF is reacted with oneequivalent of morpholine. To this solution at -40° C. is added methylester of Formula VIII and the solution is allowed to warm to 25° C. Theproduct is isolated by addition of aqueous acid and extraction intoether or methylene chloride. Evaporation of solvent and crystallizationof column chromatography on silica gel affords the pure aldehyde, XI.

Aldehydes of Formula XI may also be prepared from the esters of FormulaVIII by treatment with diisobutylaluminum hydride according toprocedures of E. Winterfeldt, Synthesis, 617 (1975).

The preparation of compounds of Formula II where R₁ ═R₂ ═CH₃ may beprepared as shown in Equation 10. ##STR24##

Compounds of Formula XII are prepared by the reaction of an excess ofmethyl lithium with acetophenones of Formula IX.

Compounds of Formula IX are restricted to structures in which thesubstituents R, Z, X and Y contain no displaceable halogens, NO₂ or CN.

An excess of methyl lithium in a suitable solvent such as diethyl ether,hexane, pentane or benzene is added to a solution or slurry of IX in asimilar solvent at temperatures between -100° and 0° C. The mixture isallowed to warm to room temperature and stir for 30 minutes. Aqueousacid is then added and the compound XII is extracted into a suitablesolvent to free it from salts followed by evaporation of the solvent.Purification is by chromatography on silica gel.

Some of the compounds of Formula I, where Z is CH or N, can also beprepared by the method described in Equation 11. ##STR25## wherein R, R₁and R₂ are as described in Formula I, X is C₁ -C₃ alkoxy and L is notOH.

Reaction Step (11a)

In Reaction Step (11a), an aromatic sulfonamide of Formula XIII iscontacted with a heterocyclic isocyanate of Formula XIV to yield anN-(haloheterocyclicaminocarbonyl)aromatic sulfonamide of Formula XV.

The heterocyclic isocyanates used in Reaction (11a) may be preparedaccording to methods described in Swiss Pat. No. 579,062, U.S. Pat. No.3,919,228, U.S. Pat. No. 3,732,223 and Angew Chem. Int. Ed. 10, 402(1976), the disclosures of which are herein incorporated by reference.

The aromatic sulfonamide and the heterocyclic isocyanate are contactedin the presence of an inert organic solvent, for example, acetonitrile,tetrahydrofuran (THF), toluene, acetone or butanone. Optionally, acatalytic amount of a base, such as 1,4-diazabicyclo[2.2.2]octane(DABCO), potassium carbonate, sodium hydride or potassium tert-butoxide,may be added to the reaction mixture. The quantity of base constitutinga catalytic amount would be obvious to one skilled in the art. Thereaction mixture is preferably maintained at a temperature of about 25°to 110° C., and the product can generally be recovered by cooling andfiltering the reaction mixture. For reasons of efficiency and economy,the preferred solvents are acetonitrile and THF, and the preferredtemperature range is about 60° to 85° C.

Reaction Steps (11b) and (11c)

In Reaction Steps (11b) and (11c), one or two of the halogen atoms onthe heterocyclic ring of the compound of Formula XV is displaced by anucleophilic species. Generally, this may be done by contacting thecompound of Formula XV either with alkanol or with alkoxide as describedby X where X is C₁₋₃ alkoxy.

Thus, in Reaction Step (11b), a compound of Formula XV, substituted withone displaceable group can be contacted with at least one equivalent ofalkanol. This reaction is sluggish, however, and it is preferred tocontact the compound of Formula XV with at least two equivalents ofalkoxide. The alkoxide can be provided in a number of ways.

(a) The compound of Formula XV can be suspended or dissolved in analkanol solvent in the presence of at least two equivalents of alkoxide.The alkoxide can be added directly as alkali metal or alkaline earthmetal alkoxide or can be generated by the addition to the alkanolsolvent of at least two equivalents of a base capable of generatingalkoxide from the solvent. Suitable bases include, but are not limitedto, the alkali and alkaline earth metals, their hydrides andtert-butoxides. For example, when X is methoxy, the compound of FormulaXV could be suspended or dissolved in methanol in the presence of twoequivalents of sodium methoxide. Alternatively, two equivalents ofsodium hydride could be used in place of the sodium methoxide.

(b) The compound of Formula XV can be suspended or dissolved in an inertsolvent in the presence of at least two equivalents of alkoxide.Suitable inert solvents include, but are not limited to, acetonitrile,THF and dimethylformamide. The alkoxide may be added directly as alkalimetal or alkaline earth metal alkoxide or may be generated from alkanoland a base as described in (a) above. For example, when X is methoxy,the compound of Formula XV could be suspended or dissolved in THF in thepresence of two equivalents of sodium methoxide. Alternatively, twoequivalents each of methanol and sodium hydride could be used instead ofsodium methoxide.

For reasons of economy and efficiency, procedure (a) is the morepreferred method.

It should be noted that two equivalents of alkoxide are required forReaction Step (b) whereas only one equivalent of alkanol is needed forthe same process. This difference is due to the reaction which isbelieved to occur between the alkoxide and the sulfonyl nitrogen of thesulfonamide of Formula XV. When alkoxide is used, the first equivalentof alkoxide removes a proton from the sulfonyl nitrogen, and is only thesecond equivalent which effects displacement of the halogen. As aresult, two equivalents of alkoxide are required. The resulting saltmust be acidified, e.g., with sulfuric, hydrochloric or acetic acid, toyield a compound of Formula XVI. Applicant, of course, does not intendto be bound by the mechanism described above.

In Reaction Step (11c) a compound of Formula XVI, is contacted witheither one equivalent of methanol or with two equivalents of methoxide.When methoxide is used, it may be provided in either of the methodsdescribed above in connection with Reaction Step (11b) and the resultingsalt can be acidified to yield a compound of Formula XVII.

When X═OCH₃, Reaction Steps (11b) and (11c) may be combined. Thus, acompound of Formula XV may be contacted either with at least twoequivalents of methanol or with at least three equivalents of methoxide.

For a compound of Formula XV, certain reaction conditions will favordisplacement of only one of the chlorine groups. These conditions arethe use of low temperatures and, when alkoxide is used, the slowaddition of the stoichiometric amount of alkoxide or alkoxide-generatingbase to the medium containing the compound of Formula XV.

When alkoxide is used, both Reaction Steps (11b) and (11c) arepreferably run at temperatures within the range of about -10° C., therange of about 0° to 25° C. being more preferred. Reaction Steps (11b)and (11c) are more sluggish when alkanol is used instead of alkoxide,and more drastic conditions are required for the reaction to go tocompletion. Thus, higher temperatures, up to and including the boilingpoint of the alkanol itself, are required.

Depending on the nature of L in the compounds of Formula XIII, theconversion to compounds of Formula XVII by the reactions described inEquation 11 is carried out without alteration of L. In other cases, thereactions result in the hydrolysis of the benzyl alcohol derivatives togive compounds of Formula XVIII wherein L is OH. Other compounds ofFormula I may then be prepared by the methods previously described.

Thus, the reaction sequence described in Equation 12 shows a protected2-hydroxymethylbenzenesulfonamide converted to a useful herbicide viareaction with a heterocyclic isocyanate. ##STR26##

As shown in Equation 13, compounds of Formula I wherein W is S areprepared by the reaction of an appropriately substitutedbenzenesulfonamide with the appropriate triazine or pyrimidineisothiocyanate of formula XXI. ##STR27## The reaction of Equation 13 isbest carried out by dissolving or suspending the sulfonamide andisothiocyanate in a polar solvent such as acetone, acetonitrile, ethylacetate or methylethylketone, adding an equivalent of a base such aspotassium carbonate and stirring the mixture at ambient temperature upto the reflux temperature for 1 to 24 hours. In some cases, the productprecipitates from the reaction mixture and can be removed by filtration.The product is stirred in dilute mineral acid, filtered and washed withcold water. If the product does not precipitate from the reactionmixture, it can be isolated by evaporation of the solvent, triturationof the residue with dilute mineral acid and filtering off the insolubleproduct.

The heterocyclic isothiocyanates which are used in the procedure ofEquation 13 are prepared, for example, according to the method of Japanpatent Application Pub.: Kokai No. 51-143686, June 5, 1976, or that ofW. Abraham and G. Barnikow, Tetrahedron, 29, 691-697 (1973).

From the above, it is seen that compounds of Formula XX are usefulintermediates in the preparation of compounds of this invention.

Compounds of Formula XVIII can be prepared via a series of standardfunctional group transformations as (J. F. King, A. Hawson, B. L.Huston, L. J. Danks, and J. Komery, Can. J. Chem. 49, 943 (1971) for2-(chloromethyl)benzenesulfonyl chloride. ##STR28##

Conversion of sulfonyl chlorides to sulfonamides is well known, e.g.,Crossley et al., J. Am. Chem. Soc., 60, 2223 (1938).

For those examples containing reactive functionality on the positionortho to the sulfonamide moiety it is convenient to add the sulfonylchloride to a measured quantity of ammonia in an inert solvent, e.g.,tetrahydrofuran, ethyl acetate, etc. at low temperatures (-78°-0°). Sidereactions such as ring formation, elimination or condensation arethereby substantially avoided. ##STR29##

The α-haloalkylbenzenesulfonamide may be converted to other requiredintermediates for this invention by treatment which appropriatenucleophiles, e.g., acetate ion as described in Example 4. ##STR30##

Thus, compounds of Formula XVIII are useful intermediates in thepreparation of compounds of this invention.

The synthesis of heterocyclic amines has been reviewed in "The Chemistryof Heterocyclic Compounds" a series published by Interscience Publ., NewYork and London. 2-Aminopyrimidines are described by D. J. Brown in ThePyrimidines, Vol. XVI of this series. The 2-amino-1,3,5-triazines arereviewed by K. R. Huffman and in The Triazines of this same series. Thesynthesis of triazines are also described by F. C. Schaefer, U.S. Pat.No. 3,154,547 and by K. R. Huffman and F. C. Schaeffer, J. Org. Chem.28, 1816-1821 (1963).

The preparation of the aminoheterocycles described by the followingformulae are prepared by methods described in unexamined European Pat.No. 15683. ##STR31##

Agriculturally suitable salts of compounds of Formula I are also usefulherbicides and can be prepared by a number of ways known to the art. Forexample, metal salts can be made by treating compounds of Formula I witha solution of alkali or alkaline earth metal salt having a sufficientlybasic anion (e.g., hydroxide, alkoxide, carbonate or hydride).Quaternary amine salts can be made by similar techniques.

Salts of compounds of Formula I can also be prepared by exchange of onecation to another. Cationic exchange can be effected by direct treatmentof an aqueous solution of a salt of a compound of Formula I (e.g.,alkali metal or quaternary amine salt) with a solution containing thecation to be exchanged. This method is most effective when the desiredsalt containing the exchanged cation is insoluble in water, e.g., acopper salt, and can be separated by filtration.

Exchange may also be effected by passing an aqueous solution of a saltof a compound of Formula I (e.g., an alkali metal or quaternary aminesalt) through a column packed with a cation exchange resin containingthe cation to be exchanged. In this method, the cation of the resin isexchanged for that of the original salt and the desired product iseluted from the column. This method is particularly useful when thedesired salt is water soluble, e.g., a potassium, sodium or calciumsalt.

Acid addition salts, useful in this invention, can be obtained byreacting a compound of Formula I with a suitable acid, e.g.,p-toluenesulfonic acid, trichloroacetic acid or the like.

The compounds of this invention and their preparation are furtherillustrated by the following examples wherein temperatures are given indegrees centigrade and all parts are by weight unless otherwiseindicated.

EXAMPLE 1N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-2-carboxybenzenesulfonamide

A mixture containing 5 g ofN-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide,20 ml of ethanol, 2.5 ml of water and 2.5 g of potassium hydroxide wasstirred at ambient temperature and pressure for 18 hours. The mixturewas then diluted with 250 ml of water and 20 ml of concentratedhydrochloric acid was added with stirring. The precipitate was filteredand washed with water and dried to yield 4.85 g of the desired product,melting at 161°-2° C. The infrared absorption peaks at 3500, 3400 and1700 cm⁻¹ are consistent with the desired structure and the nuclearmagnetic resonance absorption peaks at 3.95 ppm, S, 6H, OCH₃ ofpyrimidine; 5.8 ppm S, 1H, pyrimidine proton at position 5; and 7.6-8.3ppm, M, 4H, aromatic protons, are consistent with the desired structure.

EXAMPLE 2N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(hydroxymethyl)benzenesulfonamide

To a solution of 3.9 g of N-[(4,6-dimethoxypyrimidin-b2-yl)aminocarbonyl]-2-carboxybenzenesulfonamide in 100 ml oftetrahydrofuran was added 50 ml of a 1 M solution of borane, THF complexat 25° C. The mixture was stirred at 25° C. for 18 hours followed byaddition of water and HCl. The mixture was extracted with methylenechloride and the desired product crystallized from solution, 1.1 g 29%yield, m.p. 149°-150° C. The infrared absorption peaks at 3300 cm⁻¹ and1720 cm⁻¹ are consistent with the desired structure and the nuclearmagnetic resonance absorption peaks at 3.95 ppm, S, 6H, OCH₃ ofpyrimidine; 4.9 ppm, S, 2H, benzyl protons; 5.9 ppm, S, 1H, pyrimidineproton at position 5; and 7.4-8.3 ppm, Multiplet, 4H, aromatic protonsare consistent with the desired structure.

EXAMPLE 3N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-2-methylcarbonylbenzenesulfonamide

A mixture containing 0.85 g ofN-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-carboxybenzenesulfonamidein 50 ml of anhydrous tetrahydrofuran was treated with 40 ml of 1.4molar solution of methyl lithium (low halide, Aldrich) in ether at 25°under a nitrogen atmosphere. The mixture was stirred for 4 hours at 25°and was then poured into 500 ml of water containing 10 ml ofconcentrated hydrochloric acid. The precipitated oil was extracted intomethylene chloride and the oil on evaporation of solvent was purified bypreparative thin layer chromatography on silica gel (Analtec, 2000micron, 20×20 plates) by elution with ethyl acetate/hexane in a one toone ratio. The isolated product was recrystallized from a 1-chlorobutaneand hexane mixture to give 0.1 g, m.p. 126°-8°. The infrared absorptionshowed a broadened carbonyl peak at 1710 cm⁻¹, and the absence of the3500 and 3400 cm⁻¹ peaks of the starting material. The nuclear magneticresonance spectrum showed peaks at 2.6 ppm S, 3H, ##STR32## 4.0 ppm, S,6H, CH₃ O of pyrimidine; 5.7 ppm S, 1H, pyrimidine proton at position 5;and 7.3-7.7 ppm and 8.0 ppm M, 4H, aromatic, which are constitent withthe desired structure.

EXAMPLE 4N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(α-hydroxyethyl)benzenesulfonamide

A mixture containing 1.0 g ofN-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-methylcarbonylbenzenesulfonamidein 50 ml of anhydrous THF is treated with 0.1 g of lithium aluminumhydride at 25° under a nitrogen atmosphere. The mixture is stirred for 4hours at 25° and is then poured into 500 ml of water containing 10 ml ofconcentrated hydrochloric acid. The precipitated oil is extracted intomethylene chloride and the solid on evaporation is purified by columnchromatography on silica gel.

EXAMPLE 5 2-(Acetoxymethyl)benzenesulfonamide

A mixture of 2-(chloromethyl)benzenesulfonamide (2.00 g), potassiumacetate (6.0 g) and water (75 ml) was heated to reflux for 1.5 hour. ThepH was adjusted to ca. 5.0 by addition of hydrochloric acid and thechilled mixture was filtered to give 1.05 of of shiny white solid, m.p.131°-133°. 'H NMR δ(CD₃)₂ CO 8.00-7.83 (M), 7.60-7.25 (M), 6.55 (brd s),5.47 (s), 2.97 (brd s), 2.10 (s), consistent with the assignedstructure.

EXAMPLE 62-(Acetoxymethyl)-N-[(4,6-dichloro-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamide

A solution of 4,6-dichloro-1,3,5-triazin-2-yl isocyanate (0.87 g, 4.5mmol) in acetonitrile (9 ml) was treated with2-(acetoxymethyl)benzenesulfonamide (1.04 g, 4.5 mmol) and stirred for16 hours. Volatiles were removed under vacuum to give a residue whose 'HNMR showed δ(CD₃)₂ CO, 8.05-7.80 (m, 1H), 7.65-7.27 (m, 3H), 6.45 (brds, 1H), 5.50 (s, 2H), 2.10 (s, 3H), consistent with the assignedstructure.

EXAMPLE 72-(Hydroxymethyl)-N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamide

The crude2-(acetoxymethyl)-N-[(4,6-dichloro-1,3,5-triazinyl)aminocarbonyl]benzenesulfonamidewas treated with methanol (10 ml) and then with a solution of sodiummethoxide (14 mmol) in methanol. The mixture was stirred at roomtemperature for 1.5 hour and evaporated. The residue was taken up inwater and filtered. The filtrate was acidified and filtered to give 0.45g of gummy solid which was recrystallized from a chloroform/acetonemixture to give 115 mg of white solid, m.p. 146°-148°(dec.). 'H NMRδDMSO-d₆ 12.2(brd s, 1H), 10.73 (s, 1H), 8.00-7.15 (m,4H), 4.80 (s and˜4.9-4.2 (brd s), 3H) 3.90 (s, 6H), consistent with the assignedstructure.

Using the procedures of Examples 1 to 7 and the proper reactants or themethods described herein, the compounds of Tables I-XII may be prepared.

                                      TABLE I                                     __________________________________________________________________________     ##STR33##                                                                    R       R.sub.1                                                                          R.sub.2                                                                          W R.sub.8                                                                           X       Y   m.p.(°C.)                              __________________________________________________________________________    H       H  H  O H   CH.sub.3                                                                              CH.sub.3                                          H       H  H  O H   OCH.sub.3                                                                             CH.sub.3                                          H       H  H  O H   OCH.sub.3                                                                             OCH.sub.3                                         H       H  CH.sub.3                                                                         O H   CH.sub.3                                                                              OCH.sub.3                                         H       H  CH.sub.3                                                                         O H   SCH.sub.3                                                                             OCH.sub.3                                         H       CH.sub.3                                                                         CH.sub.3                                                                         O H   CH.sub.3                                                                              OCH.sub.3                                         H       CH.sub.3                                                                         CH.sub.3                                                                         O H   OCH.sub.3                                                                             OCH.sub.3                                         5-F     H  H  O H   CH.sub.3                                                                              CH.sub.3                                          6-F     H  H  O H   OCH.sub.3                                                                             OCH.sub.3                                         5-Cl    H  H  O H   CH.sub.3                                                                              OCH.sub.3                                         3-Cl    H  H  O H   OCH.sub.3                                                                             CH.sub.3                                          5-NO.sub.2                                                                            H  H  O H   CH.sub.3                                                                              OCH.sub.3                                         5-NO.sub.2                                                                            H  H  O H   OCH.sub.3                                                                             OCH.sub.3                                         5-OCH.sub.3                                                                           H  H  O H   CH.sub.3                                                                              OCH.sub.3                                         5-OCH.sub.3                                                                           H  H  O H   OCH.sub.3                                                                             OCH.sub.3                                         4-CF.sub.3                                                                            H  H  O H   CH.sub.3                                                                              OCH.sub.3                                         5-CF.sub.3                                                                            H  H  O H   OCH.sub.3                                                                             OCH.sub.3                                         5-CH(CH.sub.3).sub.2                                                                  H  H  O H   OCH.sub.3                                                                             CH.sub.3                                          OCH.sub.2 CH.sub.2 CH.sub.3                                                           H  H  O H   CH.sub.3                                                                              OCH.sub.3                                         4-CH.sub.3                                                                            H  H  O H   CH.sub.3                                                  5-CH.sub.3                                                                            H  H  O H   OCH.sub.3                                                                             O                                                 H       H  H  O H   Cl      Cl                                                5-CH.sub.3                                                                            H  H  O H   Cl      Br                                                H       CH.sub.3                                                                         H  O H   Cl      Cl                                                5-OC.sub.2 H.sub.5                                                                    H  H  O H   Cl      Cl                                                5-CH.sub.3                                                                            H  H  O H   CH.sub.3 OCH.sub.2                                                                    CH.sub.3                                          5-CH.sub.3                                                                            H  H  O H   CH.sub.3 OCH.sub.2                                                                    Cl                                                 ##STR34##                                                                            H  H  O H   CH.sub.3                                                                              OCH.sub.3                                         H       H  H  O H   SCH.sub.3                                                                             OCH.sub.3                                         H       H  H  O H   Br      OCH.sub.3                                         H       H  O  O H                                                                                  ##STR35##                                                                            OCH.sub. 3                                        H       H     O H   CF.sub.3                                                                              Cl                                                H       H     O H   OC.sub.2 H.sub.5                                                                      Cl                                                H       H     S H   CH.sub.3                                                                              CH.sub.3                                          H       H     S H   CH.sub.3                                                                              OCH.sub.3                                         H       H     S H   OCH.sub.3                                                                             OCH.sub.3                                         H       H  H  O CH.sub.3                                                                          CH.sub.3                                                                              CH.sub.3                                          H       H  H  O CH.sub.3                                                                          CH.sub.3                                                                              OCH.sub.3                                         H       H  H  O CH.sub.3                                                                          OCH.sub.3                                                                             OCH.sub.3                                         H       H  H  O OCH.sub.3                                                                         CH.sub.3                                                                              CH.sub.3                                          H       H  H  O OCH.sub.3                                                                         CH.sub.3                                                                              OCH.sub.3                                         H       H  H  O OCH.sub.3                                                                         OCH.sub.3                                                                             OCH.sub.3                                         __________________________________________________________________________

                                      TABLE II                                    __________________________________________________________________________     ##STR36##                                                                    R        R.sub.1                                                                          R.sub.2                                                                          W R.sub.8                                                                           X       Y   Z         m.p. (°C.)                  __________________________________________________________________________    H        H  H  O H   CH.sub.2                                                                              CH.sub.3                                                                          CH                                           H        H  H  O H   CH.sub.3                                                                              OCH.sub.3                                                                         CH                                           H        H  H  O H   OCH.sub.3                                                                             OCH.sub.3                                                                         CH                                           H        H  CH.sub.3                                                                         O H   CH.sub.3                                                                              CH.sub.3                                                                          CH                                           H        H  CH.sub.3                                                                         O H   CH.sub.3                                                                              OCH.sub.3                                                                         CH                                           H        H  CH.sub.3                                                                         O H   OCH.sub.3                                                                             OCH.sub.3                                                                         CH                                           H        CH.sub.3                                                                         CH.sub.3                                                                         O H   CH.sub.3                                                                              CH.sub.3                                                                          CH                                           H        CH.sub.3                                                                         CH.sub.3                                                                         O H   CH.sub.3                                                                              OCH.sub.3                                                                         CH                                           H        CH.sub.3                                                                         CH.sub.3                                                                         O H   OCH.sub.3                                                                             OCH.sub.3                                                                         CH                                           5-F      H  H  O H   CH.sub.3                                                                              CH.sub.3                                                                          CH                                           5-F      H  H  O H   CH.sub.3                                                                              OCH.sub.3                                                                         CH                                           5-F      H  H  O H   OCH.sub.3                                                                             OCH.sub.3                                                                         CH                                           5-Cl     H  H  O H   CH.sub.3                                                                              CH.sub.3                                                                          CH                                           6-Cl     H  H  O H   CH.sub.3                                                                              OCH.sub.3                                                                         CH                                           5-Cl     H  H  O H   OCH.sub.3                                                                             OCH.sub.3                                                                         CH                                           5-NO.sub.2                                                                             H  H  O H   CH.sub.3                                                                              CH.sub.3                                                                          CH                                           5-NO.sub.2                                                                             H  H  O H   CH.sub.3                                                                              OCH.sub.3                                                                         CH                                           5-NO.sub.2                                                                             H  H  O H   OCH.sub.3                                                                             OCH.sub.3                                                                         CH                                           5-OCH.sub.3                                                                            H  H  O H   CH.sub.3                                                                              CH.sub.3                                                                          CH                                           4-OCH.sub.3                                                                            H  H  O H   CH.sub.3                                                                              OCH.sub.3                                                                         CH                                           5-OCH.sub.3                                                                            H  H  O H   OCH.sub.3                                                                             OCH.sub.3                                                                         CH                                           5-CF.sub.3                                                                             H  H  O H   CH.sub.3                                                                              CH.sub.3                                                                          CH                                           5-CF.sub.3                                                                             H  H  O H   CH.sub.3                                                                              OCH.sub.3                                                                         CH                                           3-CF.sub.3                                                                             H  H  O H   OCH.sub.3                                                                             OCH.sub.3                                                                         CH                                           H        H  H  O H   H       CH.sub.3                                                                          CCl                                          H        H  H  O H   CH.sub.3                                                                              CH.sub.3                                                                          CCN                                          H        H  H  O H   CH.sub.3                                                                              CH.sub.3                                                                          CCH.sub.3                                    H        H  H  O H   H       CH.sub.3                                                                          CCH.sub.3                                    H        H  H  O H   CH.sub.3                                                                              CH.sub.3                                                                          CCH.sub.2 CH.sub.3                           H        H  H  O H   H       CH.sub.3                                                                          CCH.sub.2 CH.sub.3                           H        H  H  O H   H       CH.sub.3                                                                          CCH.sub.2 CH.sub.2 Cl                        H        H  H  O H   CH.sub.3                                                                              CH.sub.3                                                                          CCH.sub.2 CH.sub.2 Cl                        H        H  H  O H   CH.sub.3                                                                              CH.sub.3                                                                          CCH.sub.2 CHCH.sub.2                         H        H  H  O H   H       CH.sub.3                                                                          CCH.sub.2 CHCH.sub.2                         5-OCH.sub.2 CH.sub.2 CH.sub.3                                                          H  H  O H   CH.sub.3                                                                              CH.sub.3                                                                          CH                                           5-CH.sub.2 CH.sub.2 CH.sub.3                                                           H  H  O H   CH.sub.3                                                                              OCH.sub.3                                                                         CH                                           H        CH.sub.3                                                                         H  O H   H       CH.sub.3                                                                          CC.sub.2 H.sub.5                             H        CH.sub.3                                                                         CH.sub.3                                                                         O H   H       OCH.sub.3                                                                         CCl                                          H        H  H  S H   CH.sub.3                                                                              CH.sub.3                                                                          CH                                           H        H  H  S H   CH.sub.3                                                                              OCH.sub.3                                                                         CH                                           H        H  H  S H   OCH.sub.3                                                                             OCH.sub.3                                                                         CH                                           H        H  H  O CH.sub.3                                                                          CH.sub.3                                                                              CH.sub.3                                                                          CH                                           H        H  H  O CH.sub.3                                                                          CH.sub.3                                                                              OCH.sub.3                                                                         CH                                           H        H  H  O CH.sub.3                                                                          OCH.sub.3                                                                             OCH.sub.3                                                                         CH                                           H        H  H  O OCH.sub.3                                                                         CH.sub.3                                                                              CH.sub.3                                                                          CH                                           H        H  H  O OCH.sub.3                                                                         CH.sub.3                                                                              OCH.sub.3                                                                         CH                                           H        H  H  O OCH.sub.3                                                                         OCH.sub.3                                                                             OCH.sub.3                                                                         CH                                           5-CH.sub.3                                                                             H  H  O H   CH.sub.3                                                                              OCH.sub.3                                                                         CH                                           4-CH.sub.3                                                                             H  H  O H   OCH.sub.3                                                                             OCH.sub.3                                                                         CH                                           H        H  H  O H   Cl      Cl  CH                                           H        CH.sub.3                                                                         H  O H   Cl      Cl  CH                                           5-OC.sub.2 H.sub.5                                                                     H  H  O H   Cl      Cl  CH                                            ##STR37##                                                                             H  H  O H   CH.sub.2 OCH.sub.3                                                                    CH.sub.3                                                                          CH                                           H        H  H  O H   CH.sub.2 OCH.sub.3                                                                    CH.sub.3                                                                          CH                                           H        H  H  O H   SCH.sub.3                                                                             OCH.sub.3                                                                         CH                                           H        H  H  O H   SCH.sub.3                                                                             CH.sub.3                                                                          CH                                           H        H  H  O H   SCH.sub.3                                                                             Cl  CH                                           H        H  H  O H   CF.sub.3                                                                              Cl  CH                                           H        H  H  O H                                                                                  ##STR38##                                                                            OCH.sub.3                                                                         CH                                           H        H  CH.sub.3                                                                         O H   OC.sub.2 H.sub.5                                                                      OCH.sub.3                                                                         CH                                           H        H  H  O H   CF.sub.3                                                                              CH.sub.3                                                                          CH                                           __________________________________________________________________________

                  TABLE III                                                       ______________________________________                                         ##STR39##                                                                                                                 m.p.                             R          R.sub.1                                                                              R.sub.2                                                                              W   R.sub.8                                                                            Y'    Q    (°C.)                     ______________________________________                                        H          H      H      O   H    CH.sub.3                                                                            O                                     H          H      H      O   H    OCH.sub.3                                                                           O                                     H          H      CH.sub.3                                                                             O   H    CH.sub.3                                                                            O                                     H          H      CH.sub.3                                                                             O   H    OCH.sub.3                                                                           O                                     H          CH.sub.3                                                                             CH.sub.3                                                                             O   H    CH.sub.3                                                                            O                                     H          CH.sub.3                                                                             CH.sub.3                                                                             O   H    OCH.sub.3                                                                           O                                     5-F        H      H      O   H    OCH.sub.3                                                                           O                                     5-Cl       H      H      O   H    OCH.sub.3                                                                           O                                     5-CH.sub.3 H      H      O   H    OCH.sub.3                                                                           O                                     5-NO.sub.2 H      H      O   H    OCH.sub.3                                                                           O                                     5-OCH.sub.3                                                                              H      H      O   H    OCH.sub.3                                                                           O                                     5-Cl       H      H      O   H    CH.sub.3                                                                            O                                     H          H      H      O   H    H     CH.sub.2                              H          H      H      O   H    Cl    CH.sub.2                              H          H      H      O   H    CH.sub.3                                                                            CH.sub.2                              H          H      H      O   H    OCH.sub.3                                                                           CH.sub.2                              H          H      H      O   H    H     O                                     5-CH.sub.3 H      H      O   H    OCH.sub.3                                                                           O                                      ##STR40## H      H      O   H    OCH.sub.3                                                                           O                                     5-OC.sub.2 H.sub.5                                                                       H      H      O   H    CH.sub.3                                                                            O                                     4-CH.sub.3 H      H      O   H    Cl    O                                     4-OCH.sub.2 CH.sub.2 CH.sub.3                                                            H      H      O   H    OCH.sub.3                                                                           O                                     H          H      H      S   H    CH.sub.3                                                                            O                                     H          H      H      S   H    CH.sub.3                                                                            CH.sub.2                              H          H      H      S   H    OCH.sub.3                                                                           O                                     H          H      H      S   H    OCH.sub.3                                                                           CH.sub.2                              H          H      H      O   CH.sub.3                                                                           CH.sub.3                                                                            O                                     H          H      H      O   CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2                              H          H      H      O   CH.sub.3                                                                           OCH.sub.3                                                                           O                                     H          H      H      O   CH.sub.3                                                                           OCH.sub.3                                                                           CH.sub.2                              H          H      H      O   H    OC.sub.2 H.sub.5                                                                    O                                     H          H      H      O   H    OC.sub. 2 H.sub.5                                                                   CH.sub.2                              ______________________________________                                    

                  TABLE IIIa                                                      ______________________________________                                         ##STR41##                                                                    R           R.sub.1                                                                              R.sub.2                                                                              W    R.sub.8                                                                            Y'    m.p.(°C.)                    ______________________________________                                        H           H      H      O    H    CH.sub.3                                  H           H      H      O    H    OCH.sub.3                                 H           H      CH.sub.3                                                                             O    H    CH.sub.3                                  H           H      CH.sub.3                                                                             O    H    OCH.sub.3                                 H           CH.sub.3                                                                             CH.sub.3                                                                             O    H    CH.sub.3                                  H           CH.sub.3                                                                             CH.sub.3                                                                             O    H    OCH.sub.3                                 5-F         H      H      O    H    OCH.sub.3                                 5-Cl        H      H      O    H    OCH.sub.3                                 5-CH.sub.3  H      H      O    H    OCH.sub.3                                 5-NO.sub.2  H      H      O    H    OCH.sub.3                                 5-OCH.sub.3 H      H      O    H    OCH.sub.3                                 5-Cl        H      H      O    H    CH.sub.3                                  H           H      H      O    H    H                                         H           H      H      O    H    Cl                                        H           H      H      O    H    CH.sub.3                                  H           H      H      O    H    OCH.sub.3                                 H           H      H      O    H    H                                         5-CH.sub.3  H      H      O    H    OCH.sub.3                                  ##STR42##  H      H      O    H    OCH.sub.3                                 5-OC.sub.2 H.sub.5                                                                        H      H      O    H    CH.sub.3                                  4-CH.sub.3  H      H      O    H    Cl                                        4-OCH.sub.2 CH.sub.2 CH.sub.3                                                             H      H      O    H    OCH.sub.3                                 H           H      H      S    H    CH.sub.3                                  H           H      H      S    H    CH.sub.3                                  H           H      H      S    H    OCH.sub.3                                 H           H      H      S    H    OCH.sub.3                                 H           H      H      O    CH.sub.3                                                                           CH.sub.3                                  H           H      H      O    CH.sub.3                                                                           CH.sub.3                                  H           H      H      O    CH.sub.3                                                                           OCH.sub.3                                 H           H      H      O    CH.sub.3                                                                           OCH.sub.3                                 H           H      H      O    H    OC.sub.2 H.sub.5                          H           H      H      O    H    OC.sub.2 H.sub.5                          ______________________________________                                    

                                      TABLE IV                                    __________________________________________________________________________     ##STR43##                                                                    R       R.sub.1                                                                          R.sub.2                                                                          R.sub.11 W R.sub.8                                                                           X      Y   m.p.(°C.)                      __________________________________________________________________________    H       H  H  H        O H   CH.sub.3                                                                             CH.sub.3                                  H       H  H  H        O H   CH.sub.3                                                                             OCH.sub.3                                 H       H  H  H        O H   OCH.sub.3                                                                            OCH.sub.3                                 H       H  H  CH.sub.3 O H   CH.sub.3                                                                             CH.sub.3                                  H       H  H  CH.sub.3 O H   CH.sub.3                                                                             OCH.sub.3                                 H       H  H  CH.sub.3 O H   OCH.sub.3                                                                            OCH.sub.3                                 H       H  H  CH.sub.2 CH.sub.3                                                                      O H   CH.sub.3                                                                             OCH.sub.3                                 H       H  H  CH.sub.2 CH.sub. 3                                                                     O H   OCH.sub.3                                                                            OCH.sub.3                                 H       H  H  CF.sub.3 O H   OCH.sub.3                                                                            OCH.sub.3                                 H       H  H  CF.sub.3 O H   CH.sub.3                                                                             OCH.sub.3                                 H       H  H  CH.sub.2 Cl                                                                            O H   CH.sub.3                                                                             OCH.sub.3                                 H       H  H  CH.sub.2 CHCH.sub.2                                                                    O H   CH.sub.3                                                                             OCH.sub.3                                 H       H  H                                                                                 ##STR44##                                                                             O H   CH.sub.3                                                                             OCH.sub.3                                 H       H  H                                                                                 ##STR45##                                                                             O H   OCH.sub.3                                                                            OCH.sub.3                                 H       H  H                                                                                 ##STR46##                                                                             O H   CH.sub.3                                                                             OCH.sub.3                                 H       H  H                                                                                 ##STR47##                                                                             O H   OCH.sub.3                                                                            OCH.sub.3                                 H       H  CH.sub.3                                                                         CH.sub.3 O H   OCH.sub.3                                                                            OCH.sub.3                                 H       CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3 O H   OCH.sub.3                                                                            OCH.sub.3                                 5-F     H  H  CH.sub.3 O H   OCH.sub.3                                                                            OCH.sub.3                                 6-Cl    H  H  CH.sub.3 O H   OCH.sub.3                                                                            OCH.sub.3                                 5-CH.sub.3                                                                            H  H  CH.sub.3 O H   OCH.sub.3                                                                            OCH.sub.3                                 5-NO.sub.2                                                                            H  H  CH.sub.3 O H   OCH.sub.3                                                                            OCH.sub.3                                 4-OCH.sub.3                                                                           H  H  CH.sub.3 O H   OCH.sub.3                                                                            OCH.sub.3                                 5-CF.sub.3                                                                            H  H  CH.sub.3 O H   OCH.sub.3                                                                            OCH.sub.3                                 3-Cl    H  H  CH.sub.3 O H   CH.sub.3                                                                             OCH.sub.3                                 6-Cl    H  H  CH.sub.3 O H   CH.sub.3                                                                             OCH.sub.3                                 H       H  H  CH.sub.3 O H   Cl     Cl                                        H       H  H  CH.sub.3 O H   Cl     OCH.sub.3                                 H       H  H  CH.sub.3 O H   Br     OCH.sub.3                                 H       H  H  CH.sub.3 O H   CH.sub.2 CH.sub.3                                                                    OCH.sub.3                                 H       H  H  CH.sub.3 O H   OCH.sub.2 CH.sub.3                                                                   CH.sub.3                                  H       H  H  CH.sub.3 O H   OCH(CH.sub.3).sub.2                                                                  CH.sub.3                                  H       H  H  CH.sub.3 O H   CF.sub.3                                                                             OCH.sub.3                                 H       H  H  CH.sub.3 O H   SCH.sub.3                                                                            OCH.sub.3                                 H       H  H  CH.sub.3 O H   CH.sub.2 OCH.sub.3                                                                   CH.sub.3                                  H       H  H  CH.sub.3 O H   CH.sub.2 OCH.sub.3                                                                   OCH.sub.3                                 H       H  H  CH.sub.3 O H   H      CH.sub.3                                  H       H  H  CH.sub.3 O H   H      OCH.sub.3                                 H       H  H                                                                                 ##STR48##                                                                             O H   Cl     Cl                                        H       H  H                                                                                 ##STR49##                                                                             O H   OCH.sub.3                                                                            OCH.sub.3                                 H       H  H  CHCH.sub.2                                                                             O H   CH.sub.3                                                                             OCH.sub.3                                 H       H  H  CCH      O H   CH.sub.3                                                                             OCH.sub.3                                 H       H  H  CCCH.sub.3                                                                             O H   OCH.sub.3                                                                            CH.sub.3                                  H       H  H  (n-C.sub.5 H.sub.11)                                                                   O H   OCH.sub.3                                                                            CH.sub.3                                  H       H  H  CH.sub.2 OCH.sub.3                                                                     O H   OCH.sub.3                                                                            CH.sub.3                                  H       H  H                                                                                 ##STR50##                                                                             O H   OCH.sub.3                                                                            OCH.sub.3                                 H       H  H                                                                                 ##STR51##                                                                             O H   OCH.sub.3                                                                            CH.sub.3                                  H       H  H  CH.sub.3 O H   SCH.sub.3                                                                            OCH.sub.3                                 H       H  H  CH.sub.3 O H   CF.sub.3                                                                             OCH.sub.3                                  ##STR52##                                                                            H  H  CH.sub.3 O H   OCH.sub.3                                                                            CH.sub.3                                  5-OC.sub. 2 H.sub.5                                                                   H  H  CH.sub.3 O H   OCH.sub.3                                                                            OCH.sub.3                                 H       H  H  CH.sub.3 O H   Br     OCH.sub.3                                 H       H  H  CH.sub.2 OCH.sub.3                                                                     O H   SCH.sub.3                                                                            CH.sub.3                                  H       H  H                                                                                 ##STR53##                                                                             O H   SCH.sub.3                                                                            OCH.sub.3                                 H       H  H                                                                                 ##STR54##                                                                             O H   SCH.sub.3                                                                            CH.sub.3                                  H       H  H  CH.sub.3 O H   SCH.sub.3                                                                            CH.sub.3                                  H       H  H  CH.sub.3 O H   CF.sub.3                                                                             OCH.sub.3                                 H       H  H  CH.sub.3 O H   CH.sub.2 OCH.sub.3                                                                   OCH.sub.3                                 H       H  H                                                                                 ##STR55##                                                                             O H   OCH.sub.3                                                                            CH.sub.3                                  H       H  H                                                                                 ##STR56##                                                                             O H   OCH.sub.3                                                                            CH.sub.3                                  H       H  H                                                                                 ##STR57##                                                                             O H   OCH.sub.3                                                                            OCH.sub.3                                 H       H  H  CH.sub.3 S H   CH.sub.3                                                                             CH.sub.3                                  H       H  H  CH.sub.3 S H   CH.sub.3                                                                             OCH.sub.3                                 H       H  H  CH.sub.3 S H   OCH.sub.3                                                                            OCH.sub.3                                 H       H  H  CH.sub.3 O CH.sub.3                                                                          CH.sub.3                                                                             CH.sub.3                                  H       H  H  CH.sub. 3                                                                              O CH.sub.3                                                                          CH.sub.3                                                                             OCH.sub.3                                 H       H  H  CH.sub.3 O CH.sub.3                                                                          OCH.sub.3                                                                            OCH.sub.3                                 H       H  H  CH.sub.3 O OCH.sub.3                                                                         CH.sub.3                                                                             CH.sub.3                                  H       H  H  CH.sub.3 O OCH.sub.3                                                                         CH.sub.3                                                                             OCH.sub.3                                 H       H  H  CH.sub.3 O OCH.sub.3                                                                         OCH.sub.3                                                                            OCH.sub.3                                 __________________________________________________________________________

                                      TABLE V                                     __________________________________________________________________________     ##STR58##                                                                    R      R.sub.1                                                                          R.sub.2                                                                          R.sub.11                                                                              W R.sub.8                                                                           X      Y   Z         m.p.(°C.)              __________________________________________________________________________    H      H  H  H       O H   CH.sub.3                                                                             CH.sub.3                                                                          CH                                      H      H  H  H       O H   CH.sub.3                                                                             OCH.sub.3                                                                         CH                                      H      H  H  H       O H   OCH.sub.3                                                                            OCH.sub.3                                                                         CH                                      H      H  H  CH.sub.3                                                                              O H   CH.sub.3                                                                             CH.sub.3                                                                          CH                                      H      H  H  CH.sub.3                                                                              O H   CH.sub.3                                                                             OCH.sub.3                                                                         CH                                      H      H  H  CH.sub.3                                                                              O H   OCH.sub.3                                                                            OCH.sub.3                                                                         CH                                      H      H  H  CH.sub.2 CH.sub.3                                                                     O H   CH.sub.3                                                                             OCH.sub.3                                                                         CH                                      H      H  H  CH.sub.2 CH.sub.3                                                                     O H   OCH.sub.3                                                                            OCH.sub.3                                                                         CH                                      H      H  H  CF.sub.3                                                                              O H   OCH.sub.3                                                                            OCH.sub.3                                                                         CH                                      H      H  H  CF.sub.3                                                                              O H   CH.sub.3                                                                             OCH.sub.3                                                                         CH                                      H      H  H  CH.sub.2 Cl                                                                           O H   CH.sub.3                                                                             OCH.sub.3                                                                         CH                                      H      H  H  CH.sub.2 CHCH.sub.2                                                                   O H   CH.sub.3                                                                             OCH.sub.3                                                                         CH                                      H      H  H                                                                                 ##STR59##                                                                            O H   CH.sub.3                                                                             OCH.sub.3                                                                         CH                                      H      H  H                                                                                 ##STR60##                                                                            O H   OCH.sub.3                                                                            OCH.sub.3                                                                         CH                                      H      H  H                                                                                 ##STR61##                                                                            O H   CH.sub.3                                                                             OCH.sub.3                                                                         CH                                      H      H  H                                                                                 ##STR62##                                                                            O H   OCH.sub.3                                                                            OCH.sub.3                                                                         CH                                      H      H  CH.sub.3                                                                         CH.sub.3                                                                              O H   OCH.sub.3                                                                            OCH.sub.3                                                                         CH                                      H      CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                              O H   OCH.sub.3                                                                            OCH.sub.3                                                                         CH                                      5-F    H  H  CH.sub.3                                                                              O H   OCH.sub.3                                                                            OCH.sub.3                                                                         CH                                      6-Cl   H  H  CH.sub.3                                                                              O H   OCH.sub.3                                                                            OCH.sub.3                                                                         CH                                      H      H  H                                                                                 ##STR63##                                                                            O H   OCH.sub.3                                                                            OCH.sub.3                                                                         CH                                      5-CH.sub.3                                                                           H  H  CH.sub.3                                                                              O H   OCH.sub.3                                                                            OCH.sub.3                                                                         CH                                      5-NO.sub.2                                                                           H  H  CH.sub.3                                                                              O H   OCH.sub.3                                                                            OCH.sub.3                                                                         CH                                      5-OCH.sub.3                                                                          H  H  CH.sub.3                                                                              O H   OCH.sub.3                                                                            OCH.sub.3                                                                         CH                                      5-CF.sub.3                                                                           H  H  CH.sub.3                                                                              O H   OCH.sub.3                                                                            OCH.sub.3                                                                         CH                                      4-Cl   H  H  CH.sub.3                                                                              O H   CH.sub.3                                                                             OCH.sub.3                                                                         CH                                      6-Cl   H  H  CH.sub.3                                                                              O H   CH.sub.3                                                                             OCH.sub.3                                                                         CH                                      H      H  H  CH.sub.3                                                                              O H   Cl     Cl  CH                                      H      H  H  CH.sub.3                                                                              O H   Cl     OCH.sub.3                                                                         CH                                      H      H  H  CH.sub.3                                                                              O H   Br     OCH.sub.3                                                                         CH                                      H      H  H  CH.sub.3                                                                              O H   CH.sub.2 CH.sub.3                                                                    OCH.sub.3                                                                         CH                                      H      H  H  CH.sub.3                                                                              O H   OCH.sub.2 CH.sub.3                                                                   CH.sub.3                                                                          CH                                      H      H  H  CH.sub.3                                                                              O H   OCH(CH.sub.3).sub.2                                                                  CH.sub.3                                                                          CH                                      H      H  H  CH.sub.3                                                                              O H   CF.sub.3                                                                             OCH.sub.3                                                                         CH                                      H      H  H  CH.sub.3                                                                              O H   SCH.sub.3                                                                            OCH.sub.3                                                                         CH                                      H      H  H  CH.sub.3                                                                              O H   CH.sub.2 OCH.sub.3                                                                   CH.sub.3                                                                          CH                                      H      H  H  CH.sub.3                                                                              O H   CH.sub.2 OCH.sub.3                                                                   OCH.sub.3                                                                         CH                                      H      H  H  CH.sub.3                                                                              O H   H      CH.sub.3                                                                          CH                                      H      H  H  CH.sub.3                                                                              O H   H      OCH.sub.3                                                                         CH                                      H      H  H                                                                                 ##STR64##                                                                            O H   Cl     Cl  CH                                      H      H  H                                                                                 ##STR65##                                                                            O H   OCH.sub.3                                                                            OCH.sub.3                                                                         CH                                      H      H  H  CH.sub.3                                                                              O H   H      CH.sub.3                                                                          CCl                                     H      H  H  CH.sub.3                                                                              O H   CH.sub.3                                                                             CH.sub.3                                                                          CCN                                     H      H  H  CH.sub.3                                                                              O H   CH.sub.3                                                                             CH.sub.3                                                                          CCH.sub.3                               H      H  H  CH.sub.3                                                                              O H   H      CH.sub.3                                                                          CCH.sub.3                               H      H  H  CH.sub.3                                                                              O H   CH.sub.3                                                                             CH.sub.3                                                                          CCH.sub.2 CH.sub.3                      H      H  H  CH.sub.3                                                                              O H   H      CH.sub.3                                                                          CCH.sub.2 CH.sub.3                      H      H  H  CH.sub.3                                                                              O H   Cl     Cl  CCH.sub.2 CH.sub.2 Cl                   H      H  H  CH.sub.3                                                                              O H   H      CH.sub.3                                                                          CCH.sub.2 CH.sub.2 Cl                   H      H  H  CH.sub.3                                                                              O H   CH.sub.3                                                                             CH.sub.3                                                                          CCH.sub.2 CH.sub.2 Cl                   H      H  H  CH.sub.3                                                                              O H   CH.sub.3                                                                             CH.sub.3                                                                          CCH.sub. 2 CHCH.sub.2                   H      H  H  CH.sub.3                                                                              O H   H      CH.sub.3                                                                          CCH.sub.2 CHCH.sub.2                    H      H  H  CHCH.sub.2                                                                            S H   CH.sub.3                                                                             OCH.sub.3                                                                         CH                                      H      H  H  CCCH.sub.3                                                                            S H   CH.sub.3                                                                             OCH.sub.3                                                                         CH                                      H      H  H  CCCH.sub.3                                                                            S H   OCH.sub.3                                                                            CH.sub.3                                                                          CH                                      H      H  H  (n-C.sub. 5 H.sub.11)                                                                 S H   OCH.sub.3                                                                            CH.sub.3                                                                          CH                                      H      H  H  CH.sub.2 OCH.sub.3                                                                    S H   OCH.sub.3                                                                            CH.sub.3                                                                          CH                                      H      H  H                                                                                 ##STR66##                                                                            S H   OCH.sub.3                                                                            OCH.sub.3                                                                         CH                                      H      H  H                                                                                 ##STR67##                                                                            S H   OCH.sub.3                                                                            CH.sub.3                                                                          CH                                      H      H  H  CH.sub.3                                                                              S H   SCH.sub.3                                                                            OCH.sub.3                                                                         CH                                      H      H  H  CH.sub.3                                                                              S H   CF.sub.3                                                                             OCH.sub.3                                                                         CH                                       ##STR68##                                                                           H  H  CH.sub.3                                                                              S H   OCH.sub.3                                                                            CH.sub.3                                                                          CH                                      5-C.sub.2 H.sub.5                                                                    H  H  CH.sub.3                                                                              S H   OCH.sub. 3                                                                           OCH.sub.3                                                                         CH                                      H      H  H  CH.sub.3                                                                              S H   CH.sub.2 OCH.sub.3                                                                   OCH.sub.3                                                                         CH                                      H      H  H                                                                                 ##STR69##                                                                            S H   CH.sub.3                                                                             OCH.sub.3                                                                         CH                                      H      H  H                                                                                 ##STR70##                                                                            S H   OCH.sub.3                                                                            OCH.sub.3                                                                         CH                                      H      H  H                                                                                 ##STR71##                                                                            S H   CH.sub.3                                                                             OCH.sub.3                                                                         CH                                      H      H  H                                                                                 ##STR72##                                                                            S H   CH.sub.3                                                                             OCH.sub.3                                                                         CH                                      H      H  H                                                                                 ##STR73##                                                                            S H   CH.sub.3                                                                             OCH.sub.3                                                                         CH                                      H      H  H  CH.sub.3                                                                              S H   CH.sub.3                                                                             CH.sub.3                                                                          CH                                      H      H  H  CH.sub.3                                                                              S H   CH.sub.3                                                                             OCH.sub.3                                                                         CH                                      H      H  H  CH.sub.3                                                                              S H   OCH.sub.3                                                                            OCH.sub.3                                                                         CH                                      H      H  H  CH.sub.3                                                                              O CH  CH.sub.3                                                                             CH.sub.3                                                                          CH                                      H      H  H  CH.sub.3                                                                              O CH  CH.sub.3                                                                             OCH.sub.3                                                                         CH                                      H      H  H  CH.sub.3                                                                              O CH  OCH.sub.3                                                                            OCH.sub.3                                                                         CH                                      H      H  H  CH.sub.3                                                                              O OCH CH.sub.3                                                                             CH.sub.3                                                                          CH                                      H      H  H  CH.sub.3                                                                              O OCH CH.sub.3                                                                             OCH.sub.3                                                                         CH                                      H      H  H  CH.sub.3                                                                              O OCH OCH.sub.3                                                                            OCH.sub.3                                                                         CH                                      __________________________________________________________________________

                                      TABLE VI                                    __________________________________________________________________________     ##STR74##                                                                    R    R.sub.1                                                                          R.sub.2                                                                          R.sub.11  W R.sub.8                                                                          Y'  Q  m.p.(°C.)                             __________________________________________________________________________    H    H  H  H         O H  CH.sub.3                                                                          O                                               H    H  H  H         O H  OCH.sub.3                                                                         O                                               H    H  H  CH.sub.3  O H  CH.sub.3                                                                          O                                               H    H  H  CH.sub.3  O H  OCH.sub.3                                                                         O                                               H    H  H  CH.sub.2 CH.sub.3                                                                       O H  CH.sub.3                                                                          O                                               H    H  H  CF.sub.3  O H  CH.sub.3                                                                          O                                               H    H  H  CF.sub.3  O H  OCH.sub.3                                                                         O                                               H    H  H  CH.sub.2 Cl                                                                             O H  OCH.sub.3                                                                         O                                               H    H  H  CH.sub.2 CHCH.sub.2                                                                     O H  OCH.sub.3                                                                         O                                               H    H  H                                                                                 ##STR75##                                                                              O H  CH.sub.3                                                                          O                                               H    H  H                                                                                 ##STR76##                                                                              O H  OCH.sub.3                                                                         O                                               H    H  H                                                                                 ##STR77##                                                                              O H  OCH.sub.3                                                                         O                                               H    H  CH.sub.3                                                                         CH.sub.3  O H  OCH.sub.3                                                                         O                                               H    CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3  O H  OCH.sub.3                                                                         O                                               5-F  H  H  CH.sub.3  O H  OCH.sub.3                                                                         O                                               5-Cl H  H  CH.sub.3  O H  OCH.sub.3                                                                         O                                               5-CH.sub.3                                                                         H  H  CH.sub.3  O H  OCH.sub.3                                                                         O                                               5-NO.sub.2                                                                         H  H  CH.sub.3  O H  OCH.sub.3                                                                         O                                               5-OCH.sub.3                                                                        H  H  CH.sub.3  O H  OCH.sub.3                                                                         O                                               3-CF.sub.3                                                                         H  H  CH.sub.3  O H  OCH.sub.3                                                                         O                                               5-Cl H  H  CH.sub.3  O H  CH.sub.3                                                                          O                                               6-Cl H  H  CH.sub.3  O H  CH.sub.3                                                                          O                                               H    H  H  CH.sub.3  O H  H   O                                               H    H  H  CH.sub.3  O H  H   CH.sub.2                                        H    H  H  CH.sub.3  O H  Cl  CH.sub.2                                        H    H  H  CH.sub.3  O H  CH.sub.3                                                                          CH.sub.2                                        H    H  H  CH.sub.3  O H  OCH.sub.3                                                                         CH.sub.2                                        H    H  H  CH.sub.3  S H  CH.sub.3                                                                          O                                               H    H  H  CH.sub.3  S H  OCH.sub.3                                                                         CH.sub.2                                        H    H  H  CH.sub.3  S H  CH.sub.3                                                                          O                                               H    H  H  CH.sub.3  S H  OCH.sub.3                                                                         CH.sub.2                                        H    H  H  CH.sub.3  O CH.sub.3                                                                         CH.sub.3                                                                          O                                               H    H  H  CH.sub.3  O OCH.sub.3                                                                        CH.sub.3                                                                          CH.sub.2                                        H    H  H  CH.sub.3  O CH.sub.3                                                                         OCH.sub.3                                                                         O                                               H    H  H  CH        O OCH.sub.3                                                                        OCH.sub.3                                                                         CH.sub.2                                        H    H  H  CH        O H  OC.sub.2 H.sub.5                                                                  O                                               H    H  H  CH        O H  OC.sub.2 H.sub.5                                                                  CH.sub.2                                        H    H  H  CH.sub.2 OCH.sub.3                                                                      O H  CH.sub.3                                                                          O                                               H    H  H                                                                                 ##STR78##                                                                              O H  CH.sub.3                                                                          O                                               H    H  H  CHCH.sub.2                                                                              O H  CH.sub.3                                                                          O                                               H    H  H                                                                                 ##STR79##                                                                              O H  CH.sub.3                                                                          O                                               H    H  H  (n-C.sub.5 H.sub.11)                                                                    O H  CH.sub. 3                                                                         O                                               5-CH.sub.3                                                                         H  H                                                                                 ##STR80##                                                                              O H  CH.sub.3                                                                          O                                               4-OC.sub.2 H.sub.5                                                                 H  H  CHCH.sub.2                                                                              O H  CH.sub.3                                                                          O                                               4-CH.sub.3                                                                         H  H  CH.sub.3  O H  CH.sub.3                                                                          CH.sub.2                                        H    H  H                                                                                 ##STR81##                                                                              O H  CH.sub.3                                                                          O                                               H    H  H                                                                                 ##STR82##                                                                              O H  CH.sub.3                                                                          O                                               H    H  H                                                                                 ##STR83##                                                                              O H  CH.sub.3                                                                          O                                               H    H  H                                                                                 ##STR84##                                                                              O H  CH.sub.3                                                                          O                                               H    H  H                                                                                 ##STR85##                                                                              O H  CH.sub.3                                                                          O                                               H    H  H                                                                                 ##STR86##                                                                              O H  OCH.sub.3                                                                         O                                               H    H  H                                                                                 ##STR87##                                                                              O H  CH.sub.3                                                                          O                                               H    H  H   CHCl.sub.2                                                                             O H  OCH.sub.3                                                                         O                                               H    H  H  CCl.sub.3 O H  OCH.sub.3                                                                         O                                               H    H  H  CHBr.sub.2                                                                              O H  OCH.sub.3                                                                         O                                               H    H  H                                                                                 ##STR88##                                                                              O H  OCH.sub.3                                                                         O                                               H    H  H                                                                                 ##STR89##                                                                              O H  OCH.sub.3                                                                         O                                               __________________________________________________________________________

                                      TABLE VIa                                   __________________________________________________________________________     ##STR90##                                                                    R    R.sub.1                                                                          R.sub.2                                                                          R.sub.11  W R.sub.8                                                                           Y'  m.p.(°C.)                               __________________________________________________________________________    H    H  H  H         O H   CH.sub.3                                           H    H  H  H         O H   OCH.sub.3                                          H    H  H  CH.sub.3  O H   CH.sub.3                                           H    H  H  CH.sub.3  O H   OCH.sub.3                                          H    H  H  CH.sub.2 CH.sub.3                                                                       O H   CH.sub.3                                           H    H  H  CF.sub.3  O H   CH.sub.3                                           H    H  H  CF.sub.3  O H   OCH.sub.3                                          H    H  H  CH.sub.2 Cl                                                                             O H   OCH.sub.3                                          H    H  H  CH.sub.2 CHCH.sub.2                                                                     O H   OCH.sub.3                                          H    H  H                                                                                 ##STR91##                                                                              O H   CH.sub.3                                           H    H  H                                                                                 ##STR92##                                                                              O H   OCH.sub.3                                          H    H  H                                                                                 ##STR93##                                                                              O H   OCH.sub.3                                          H    H  CH.sub.3                                                                         CH.sub.3  O H   OCH.sub.3                                          H    CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3  O H   OCH.sub.3                                          5-F  H  H  CH.sub.3  O H   OCH.sub.3                                          5-Cl H  H  CH.sub.3  O H   OCH.sub.3                                          H    H  H  CH.sub.2 OCH.sub.3                                                                      O H   CH.sub.3                                           H    H  H                                                                                 ##STR94##                                                                              O H   CH.sub.3                                           H    H  H  CHCH.sub.2                                                                              O H   CH.sub.3                                           H    H  H                                                                                 ##STR95##                                                                              O H   CH.sub.3                                           H    H  H  (n-C.sub.5 H.sub.11)                                                                    O H   CH.sub.3                                           5-CH.sub.3                                                                         H  H                                                                                 ##STR96##                                                                              O H   CH.sub.3                                           4-OC.sub.2 H.sub.5                                                                 H  H  CHCH.sub.2                                                                              O H   CH.sub.3                                           4-CH.sub.3                                                                         H  H  CH.sub.3  O H   CH.sub.3                                           H    H  H                                                                                 ##STR97##                                                                              O H   CH.sub.3                                           H    H  H                                                                                 ##STR98##                                                                              O H   CH.sub.3                                           H    H  H                                                                                 ##STR99##                                                                              O H   CH.sub.3                                           H    H  H                                                                                 ##STR100##                                                                             O H   CH.sub.3                                           H    H  H                                                                                 ##STR101##                                                                             O H   CH.sub.3                                           H    H  H                                                                                 ##STR102##                                                                             O H   OCH.sub.3                                          H    H  H  CH.sub.2 CF.sub.3                                                                       O H   OCH.sub.3                                          H    H  H                                                                                 ##STR103##                                                                             O H   CH.sub.3                                           H    H  H  CHCl.sub.2                                                                              O H   OCH.sub.3                                          H    H  H  CCl.sub.3 O H   OCH.sub.3                                          H    H  H  CHBr.sub.2                                                                              O H   OCH.sub.3                                          H    H  H                                                                                 ##STR104##                                                                             O H   OCH.sub.3                                          H    H  H                                                                                 ##STR105##                                                                             O H   OCH.sub.3                                          5-CH.sub.3                                                                         H  H  CH.sub.3  O H   OCH.sub.3                                          5-NO.sub.2                                                                         H  H  CH.sub.3  O H   OCH.sub.3                                          5-OCH.sub.3                                                                        H  H  CH.sub.3  O H   OCH.sub.3                                          3-CF.sub.3                                                                         H  H  CH.sub.3  O H   OCH.sub.3                                          5-Cl H  H  CH.sub.3  O H   CH.sub.3                                           6-Cl H  H  CH.sub.3  O H   CH.sub.3                                           H    H  H  CH.sub.3  O H   H                                                  H    H  H  CH.sub.3  O H   H                                                  H    H  H  CH.sub.3  O H   Cl                                                 H    H  H  CH.sub.3  O H   CH.sub.3                                           H    H  H  CH.sub.3  O H   OCH.sub.3                                          H    H  H  CH.sub.3  S H   CH.sub.3                                           H    H  H  CH.sub.3  S H   OCH.sub.3                                          H    H  H  CH.sub.3  S H   CH.sub.3                                           H    H  H  CH.sub.3  S H   OCH.sub.3                                          H    H  H  CH.sub.3  O CH.sub.3                                                                          CH.sub.3                                           H    H  H  CH.sub.3  O OCH.sub.3                                                                         CH.sub.3                                           H    H  H  CH.sub.3  O CH.sub.3                                               H    H  H  CH.sub.3  O OCH.sub.3                                                                         OCH.sub.3                                          H    H  H  CH.sub.3  O H   OC.sub.2 H.sub.5                                   H    H  H  CH.sub.3  O H   OC.sub.2 H.sub.5                                   __________________________________________________________________________

                                      TABLE VII                                   __________________________________________________________________________     ##STR106##                                                                   R       R.sub.1                                                                          R.sub.2                                                                          R.sub.12      W  R.sub.8                                                                           X      Y   m.p. (°C.)               __________________________________________________________________________    H       H  H  H             O H    CH.sub.3                                                                             CH.sub.3                            H       H  H  H             O H    CH.sub.3                                                                             OCH.sub.3                           H       H  H  H             O H    OCH.sub.3                                                                            OCH.sub.3                           H       H  H  CH.sub.3      O H    CH.sub.3                                                                             CH.sub.3                            H       H  H  CH.sub.3      O H    CH.sub.3                                                                             OCH.sub.3                           H       H  H  CH.sub.3      O H    OCH.sub.3                                                                            OCH.sub.3                           H       H  H  CH.sub.2 CH.sub.3                                                                           O H    CH.sub.3                                                                             OCH.sub.3                           H       H  H  CH.sub.2 CH.sub.3                                                                           O H    OCH.sub.3                                                                            OCH.sub.3                           H       H  H  CH(CH.sub.3).sub.2                                                                          O H    OCH.sub.3                                                                            OCH.sub.3                           H       H  H  CH(CH.sub.3).sub.2                                                                          O H    CH.sub.3                                                                             OCH.sub.3                           H       H  H                                                                                 ##STR107##   O H    CH.sub.3                                                                             OCH.sub.3                           H       H  H  CH.sub.2 CHCH.sub.2                                                                         O H    CH.sub.3                                                                             OCH.sub.3                           H       H  H                                                                                 ##STR108##   O H    CH.sub.3                                                                             OCH.sub.3                           H       H  H                                                                                 ##STR109##   O H    OCH.sub.3                                                                            OCH.sub.3                           H       H  H                                                                                 ##STR110##   O H    CH.sub.3                                                                             OCH.sub.3                           H       H  H                                                                                 ##STR111##   O H    OCH.sub.3                                                                            OCH.sub.3                           H       H  CH.sub.3                                                                         CH.sub.3      O H    OCH.sub.3                                                                            OCH.sub.3                           H       CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3      O H    OCH.sub.3                                                                            OCH.sub.3                           5-F     H  H  CH.sub.3      O H    OCH.sub.3                                                                            OCH.sub.3                           4-Cl    H  H  CH.sub.3      O H    OCH.sub.3                                                                            OCH.sub.3                           5-CH.sub.3                                                                            H  H  CH.sub.3      O H    OCH.sub.3                                                                            OCH.sub.3                           3-NO.sub.2                                                                            H  H  CH.sub.3      O H    OCH.sub.3                                                                            OCH.sub.3                           5-OCH.sub.3                                                                           H  H  CH.sub.3      O H    OCH.sub.3                                                                            OCH.sub.3                           5-CF.sub.3                                                                            H  H  CH.sub.3      O H    OCH.sub.3                                                                            OCH.sub.3                           5-Cl    H  H  CH.sub.3      O H    CH.sub.3                                                                             OCH.sub.3                           6-Cl    H  H  CH.sub.3      O H    CH.sub.3                                                                             OCH.sub.3                           H       H  H  CH.sub.3      O H    Cl     Cl                                  H       H  H  CH.sub.3      O H    Cl     OCH.sub.3                           H       H  H  CH.sub.3      O H    Br     OCH.sub.3                           H       H  H  CH.sub.3      O H    CH.sub.2 CH.sub.3                                                                    OCH.sub.3                           H       H  H  CH.sub.3      O H    OCH.sub.2 CH.sub.3                                                                   CH.sub.3                            H       H  H  CH.sub.3      O H    OCH(CH.sub.3).sub.2                                                                  CH.sub.3                            H       H  H  CH.sub.3      O H    CF.sub.3                                                                             OCH.sub.3                           H       H  H  CH.sub.3      O H    SCH.sub.3                                                                            OCH.sub.3                           H       H  H  CH.sub.3      O H    CH.sub.2 OCH.sub.3                                                                   CH.sub.3                            H       H  H  CH.sub.3      O H    CH.sub.2 OCH.sub.3                                                                   OCH.sub.3                           H       H  H  CH.sub.3      O H    H      CH.sub.3                            H       H  H  CH.sub.3      O H    H      OCH.sub.3                           H       H  H                                                                                 ##STR112##   O H    Cl     Cl                                  H       H  H                                                                                 ##STR113##   O H    OCH.sub.3                                                                            OCH.sub.3                           H       H  H  CH.sub.2(CH.sub.2).sub.4 CH.sub.3                                                           O H    CH.sub.3                                                                             OCH.sub.3                           H       H  H  CH.sub.2CHCHCH.sub.3                                                                        O H    CH.sub.3                                                                             OCH.sub.3                           H       H  H                                                                                 ##STR114##   O H    OCH.sub.3                                                                            OCH.sub.3                           H       H  H                                                                                 ##STR115##   O H    OCH.sub.3                                                                            CH.sub.3                            H       H  H                                                                                 ##STR116##   O H    OCH.sub.3                                                                            OCH.sub.3                           H       H  H                                                                                 ##STR117##   O H    OCH.sub.3                                                                            CH.sub.3                            H       H  H                                                                                 ##STR118##   O H    OCH.sub.3                                                                            CH.sub.3                            H       H  H                                                                                 ##STR119##   O H    CH.sub.3                                                                             OCH.sub.3                           H       H  H                                                                                 ##STR120##   O H    CH.sub.3                                                                             OCH.sub. 3                          H       H  H                                                                                 ##STR121##   O H    CH.sub.3                                                                             OCH.sub.3                           H       H  H                                                                                 ##STR122##   O H    OCH.sub.3                                                                            OCH.sub.3                           H       H  H                                                                                 ##STR123##   O H    CH.sub.3                                                                             OCH.sub.3                           H       H  H                                                                                 ##STR124##   O H    OCH.sub.3                                                                            OCH.sub.3                           H       H  H                                                                                 ##STR125##   O H    OCH.sub.3                                                                            OCH.sub.3                           H       H  H                                                                                 ##STR126##   O H    OCH.sub.3                                                                            CH.sub.3                            H       H  H                                                                                 ##STR127##   O H    CH.sub.3                                                                             OCH.sub.3                           5-OC.sub.2 H.sub.5                                                                    H  H  CH.sub.3      O H    OCH.sub.3                                                                            OCH.sub.3                            ##STR128##                                                                           H  H  CH.sub.3      O H    OCH.sub.3                                                                            OCH.sub.3                           3-CF.sub.3                                                                            H  H  CH.sub.3      O H    OCH.sub.3                                                                            OCH.sub.3                           H       H  H  CH.sub.3      S H    CH.sub.3                                                                             CH.sub.3                            H       H  H  CH.sub.3      S H    CH.sub.3                                                                             OCH.sub.3                           H       H  H  CH.sub.3      S H    OCH.sub.3                                                                            OCH.sub.3                           H       H  H  CH.sub.3      O CH.sub.3                                                                           CH.sub.3                                                                             CH.sub.3                            H       H  H  CH.sub.3      O CH.sub.3                                                                           CH.sub.3                                                                             OCH.sub.3                           H       H  H  CH.sub.3      O CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                           H       H  H  CH.sub.3      O OCH.sub.3                                                                          CH.sub.3                                                                             CH.sub.3                            H       H  H  CH.sub.3      O OCH.sub.3                                                                          CH.sub.3                                                                             OCH.sub.3                           H       H  H  CH.sub.3      O OCH.sub.3                                                                          OCH.sub.3                                                                            OCH.sub.3                           __________________________________________________________________________

                                      TABLE VIII                                  __________________________________________________________________________     ##STR129##                                                                   R       R.sub.1                                                                           R.sub.2                                                                          R.sub.12      W R.sub.8                                                                            X      Y    Z         m.p.                                                                          (°C.)        __________________________________________________________________________    H       H   H  H             O H    CH.sub.3                                                                             CH.sub.3                                                                           CH                            H       H   H  H             O H    CH.sub.3                                                                             OCH.sub.3                                                                          CH                            H       H   H  H             O H    OCH.sub.3                                                                            OCH.sub.3                                                                          CH                            H       H   H  CH.sub.3      O H    CH.sub.3                                                                             CH.sub.3                                                                           CH                            H       H   H  CH.sub.3      O H    CH.sub.3                                                                             OCH.sub.3                                                                          CH                            H       H   H  CH.sub.3      O H    OCH.sub.3                                                                            OCH.sub.3                                                                          CH                            H       H   H  CH.sub.2 CH.sub.3                                                                           O H    CH.sub.3                                                                             OCH.sub.3                                                                          CH                            H       H   H   CH.sub.2 CH.sub.3                                                                          O H    OCH.sub.3                                                                            OCH.sub.3                                                                          CH                            H       H   H  CH(CH.sub.3).sub.2                                                                          O H    OCH.sub.3                                                                            OCH.sub.3                                                                          CH                            H       H   H  CH(CH.sub.3).sub.2                                                                          O H    CH.sub.3                                                                             OCH.sub.3                                                                          CH                            H       H   H                                                                                 ##STR130##   O H    CH.sub.3                                                                             OCH.sub.3                                                                          CH                            H       H   H  CH.sub.2 CHCH.sub.2                                                                         O H    CH.sub.3                                                                             OCH.sub.3                                                                          CH                            H       H   H                                                                                 ##STR131##   O H    CH.sub.3                                                                             OCH.sub.3                                                                          CH                            H       H   H                                                                                 ##STR132##   O H    OCH.sub.3                                                                            OCH.sub.3                                                                          CH                            H       H   H                                                                                 ##STR133##   O H    CH.sub.3                                                                             OCH.sub.3                                                                          CH                            H       H   H                                                                                 ##STR134##   O H    OCH.sub.3                                                                            OCH.sub.3                                                                          CH                            H       H   CH.sub.3                                                                         CH.sub.3      O H    OCH.sub.3                                                                            OCH.sub.3                                                                          CH                            H       CH.sub.3                                                                          CH.sub.3                                                                         CH.sub.3      O H    OCH.sub.3                                                                            OCH.sub.3                                                                          CH                            5-F     H   H  CH.sub.3      O H    OCH.sub.3                                                                            OCH.sub.3                                                                          CH                            5-Cl    H   H  CH.sub.3      O H    OCH.sub.3                                                                            OCH.sub.3                                                                          CH                            H       H   H                                                                                 ##STR135##   O H    OCH.sub.3                                                                            OCH.sub.3                                                                          CH                            5-CH.sub.3                                                                            H   H  CH.sub.3      O H    OCH.sub.3                                                                            OCH.sub.3                                                                          CH                            5-NO.sub.2                                                                            H   H  CH.sub.3      O H    OCH.sub.3                                                                            OCH.sub.3                                                                          CH                            5-OCH.sub.3                                                                           H   H  CH.sub.3      O H    OCH.sub.3                                                                            OCH.sub.3                                                                          CH                            4-CF.sub.3                                                                            H   H  CH.sub.3      O H    OCH.sub.3                                                                            OCH.sub.3                                                                          CH                            5-Cl    H   H  CH.sub.3      O H    CH.sub.3                                                                             OCH.sub.3                                                                          CH                            6-Cl    H   H  CH.sub.3      O H    CH.sub.3                                                                             OCH.sub.3                                                                          CH                            H       H   H  CH.sub.3      O H    Cl     Cl   CH                            H       H   H  CH.sub.3      O H    Cl     OCH.sub.3                                                                          CH                            H       H   H  CH.sub.3      O H    Br     OCH.sub.3                                                                          CH                            H       H   H  CH.sub.3      O H    CH.sub.2 CH.sub.3                                                                    OCH.sub.3                                                                          CH                            H       H   H  CH.sub.3      O H    OCH.sub.2 CH.sub.3                                                                   CH.sub.3                                                                           CH                            H       H   H  CH.sub.3      O H    OCH(CH.sub.3).sub.2                                                                  CH.sub.3                                                                           CH                            H       H   H  CH.sub.3      O H    CF.sub.3                                                                             OCH.sub.3                                                                          CH                            H       H   H  CH.sub.3      O H    SCH.sub.3                                                                            OCH.sub.3                                                                          CH                            H       H   H  CH.sub.3      O H    CH.sub.2 OCH.sub. 3                                                                  CH.sub.3                                                                           CH                            H       H   H  CH.sub.3      O H    CH.sub.2 OCH.sub.3                                                                   OCH.sub.3                                                                          CH                            H       H   H  CH.sub.3      O H    H      CH.sub.3                                                                           CH                            H       H   H  CH.sub.3      O H    H      OCH.sub.3                                                                          CH                            H       H   H                                                                                 ##STR136##   O H    Cl     Cl   CH                            H       H   H                                                                                 ##STR137##   O H    OCH.sub.3                                                                            OCH.sub.3                                                                          CH                            H       H   H  CH.sub.3      O H    H      CH.sub.3                                                                           CCl                           H       H   H  CH.sub.3      O H    CH.sub.3                                                                             CH.sub.3                                                                           CCN                           H       H   H  CH.sub.3      O H    CH.sub.3                                                                             CH.sub.3                                                                           CCH.sub.3                     H       H   H  CH.sub.3      O H    H      CH.sub.3                                                                           CCH.sub.3                     H       H   H  CH.sub.3      O H    CH.sub.3                                                                             CH.sub.3                                                                           CCH.sub.2 CH.sub.3            H       H   H  CH.sub.3      O H    H      CH.sub.3                                                                           CCH.sub.2 CH.sub.3            H       H   H  CH.sub.3      O H    Cl     Cl   CCH.sub.2 CH.sub.2 Cl         H       H   H  CH.sub.3      O H    H      CH.sub.3                                                                           CCH.sub.2 CH.sub.2 Cl         H       H   H  CH.sub.3      O H    CH.sub.3                                                                             CH.sub.3                                                                           CCH.sub.2 CH.sub.2 Cl         H       H   H  CH.sub.3      O H    CH.sub.3                                                                             CH.sub.3                                                                           CCH.sub.2 CHCH.sub.2          H       H   H  CH.sub.3      O H    H      CH.sub.3                                                                           CCH.sub.2 CHCH.sub.2          H       H   H  CH.sub.2(CH.sub.2).sub.4 CH.sub.3                                                           O H    CH.sub.3                                                                             OCH.sub.3                                                                          CH                            H       H   H  CH.sub.2CHCHCH.sub.3                                                                        O H    CH.sub.3                                                                             OCH.sub.3                                                                          CH                            H       H   H                                                                                 ##STR138##   O H    OCH.sub.3                                                                            OCH.sub.3                                                                          CH                            H       H   H                                                                                 ##STR139##   O H    OCH.sub.3                                                                            OCH.sub.3                                                                          CH                            H       H   H                                                                                 ##STR140##   O H    OCH.sub.3                                                                            CH.sub.3                                                                           CH                            H       H   H                                                                                 ##STR141##   O H    OCH.sub.3                                                                            CH.sub.3                                                                           CH                            H       H   H                                                                                 ##STR142##   O H    OCH.sub.3                                                                            CH.sub.3                                                                           CH                            H       H   H                                                                                 ##STR143##   O H    CH.sub.3                                                                             OCH.sub.3                                                                          CH                            H       H   H                                                                                 ##STR144##   O H    CH.sub.3                                                                             OCH.sub.3                                                                          CH                            H       H   H                                                                                 ##STR145##   O H    OCH.sub.3                                                                            OCH.sub.3                                                                          CH                            H       H   H                                                                                 ##STR146##   O H    CH.sub.3                                                                             OCH.sub.3                                                                          CH                            H       H   H                                                                                 ##STR147##   O H    OCH.sub.3                                                                            OCH.sub.3                                                                          CH                            H       H   H                                                                                 ##STR148##   O H    OCH.sub.3                                                                            CH.sub.3                                                                           CH                            5-OC.sub.2 H.sub.5                                                                    H   H  CH.sub.3      O H    OCH.sub.3                                                                            CH.sub.3                                                                           CH                             ##STR149##                                                                           H   H  CH.sub.3      O H    OCH.sub.3                                                                            CH.sub.3                                                                           CH                            4-C.sub.2 H.sub.5                                                                     H   H  CH.sub.3      O H    OCH.sub.3                                                                            OCH.sub.3                                                                          CH                            5-CH.sub.3                                                                            CH.sub.3                                                                          H  CH.sub.3      O H    OCH.sub.3                                                                            OCH.sub.3                                                                          CH                            H       H   H  CH.sub.3      S H    CH.sub.3                                                                             CH.sub.3                                                                           CH                            H       H   H  CH.sub.3      S H    CH.sub.3                                                                             OCH.sub.3                                                                          CH                            H       H   H  CH.sub.3      S H    OCH.sub.3                                                                            OCH.sub.3                                                                          CH                            H       H   H  CH.sub.3      O CH.sub.3                                                                           CH.sub.3                                                                             CH.sub.3                                                                           CH                            H       H   H  CH.sub.3      O CH.sub.3                                                                           CH.sub.3                                                                             OCH.sub.3                                                                          CH                            H       H   H  CH.sub.3      O CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                          CH                            H       H   H  CH.sub.3      O OCH.sub.3                                                                          CH.sub.3                                                                             CH.sub.3                                                                           CH                            H       H   H  CH.sub.3      O OCH.sub.3                                                                          CH.sub.3                                                                             OCH.sub.3                                                                          CH                            H       H   H  CH.sub.3      O OCH.sub.3                                                                          OCH.sub.3                                                                            OCH.sub.3                                                                          CH                            __________________________________________________________________________

                                      TABLE IX                                    __________________________________________________________________________     ##STR150##                                                                   R       R.sub.1                                                                          R.sub.2                                                                          R.sub.12      W  R.sub.8                                                                           Y'  Q  m.p. (°C.)                   __________________________________________________________________________    H       H  H  H             O H    CH.sub.3                                                                          O                                      H       H  H  H             O H    OCH.sub.3                                                                         O                                      H       H  H  CH.sub.3      O H    CH.sub.3                                                                          O                                      H       H  H  CH.sub.3      O H    OCH.sub.3                                                                         O                                      H       H  H  CH.sub.2 CH.sub.3                                                                           O H    CH.sub.3                                                                          O                                      H       H  H  CH(CH.sub.3).sub.2                                                                          O H    CH.sub.3                                                                          O                                      H       H  H  CH(CH.sub.3).sub.2                                                                          O H    OCH.sub.3                                                                         O                                      H       H  H                                                                                 ##STR151##   O H    OCH.sub.3                                                                         O                                      H       H  H  CH.sub.2 CHCH.sub.2                                                                         O H    OCH.sub.3                                                                         O                                      H       H  H                                                                                 ##STR152##   O H    CH.sub.3                                                                          O                                      H       H  H                                                                                 ##STR153##   O H    OCH.sub.3                                                                         O                                      H       H  H                                                                                 ##STR154##   O H    OCH.sub.3                                                                         O                                      H       H  CH.sub.3                                                                         CH.sub.3      O H    OCH.sub.3                                                                         O                                      H       CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3      O H    OCH.sub.3                                                                         O                                      3-F     H  H  CH.sub.3      O H    OCH.sub.3                                                                         O                                      5-Cl    H  H  CH.sub.3      O H    OCH.sub.3                                                                         O                                      5-CH.sub.3                                                                            H  H  CH.sub.3      O H    OCH.sub.3                                                                         O                                      5-NO.sub.2                                                                            H  H  CH.sub.3      O H    OCH.sub.3                                                                         O                                      4-OCH.sub.3                                                                           H  H  CH.sub.3      O H    OCH.sub.3                                                                         O                                      5-CF.sub.3                                                                            H  H  CH.sub.3      O H    OCH.sub.3                                                                         O                                      5-Cl    H  H  CH.sub.3      O H    CH.sub.3                                                                          O                                      6-Cl    H  H  CH.sub.3      O H    CH.sub.3                                                                          O                                      H       H  H  CH.sub.3      O H    H   O                                      H       H  H  CH.sub.3      O H    H   CH.sub.2                               H       H  H  CH.sub.3      O H    Cl  CH.sub.2                               H       H  H  CH.sub.3      O H    CH.sub.3                                                                          CH.sub.2                               H       H  H  CH.sub.3      O H    OCH.sub.3                                                                         CH.sub.2                               H       H  H  CH.sub. 3     S H    CH.sub.3                                                                          CH.sub.2                               H       H  H  CH.sub.3      S H    OCH.sub.3                                                                         O                                      H       H  H  CH.sub.3      S H    CH.sub.3                                                                          CH.sub.2                               H       H  H  CH.sub.3      S H    OCH.sub.3                                                                         O                                      H       H  H  CH.sub.3      O CH.sub.3                                                                           CH.sub.3                                                                          O                                      H       H  H  CH.sub.3      O CH.sub.3                                                                           CH.sub.3                                                                          CH.sub.2                               H       H  H  CH.sub.3      O CH.sub.3                                                                           OCH.sub.3                                                                         O                                      H       H  H  CH.sub.3      O CH.sub.3                                                                           OCH.sub.3                                                                         CH.sub.2                               H       H  H  CH.sub.3      O OCH.sub.3                                                                          CH.sub.3                                                                          O                                      H       H  H  CH.sub.3      O OCH.sub.3                                                                          CH.sub.3                                                                          CH.sub.2                               H       H  H  CH.sub.3      O OCH.sub.3                                                                          OCH.sub.3                                                                         O                                      H       H  H  CH.sub.3      O OCH.sub.3                                                                          OCH.sub.3                                                                         CH.sub.2                               H       H  H  CH.sub.3      O H    OC.sub.2 H.sub.5                                                                  O                                      H       H  H  CH.sub.3      O H    OC.sub.2 H.sub.5                                                                  CH.sub.2                               H       H  H  CH.sub.2(CH.sub.2).sub.4 CH.sub.3                                                           O H    OCH.sub.3                                                                         O                                      H       H  H  CH.sub.2CHCHCH.sub.3                                                                        O H    CH.sub.3                                                                          O                                      H       H  H                                                                                 ##STR155##   O H    OCH.sub.3                                                                         O                                      H       H  H                                                                                 ##STR156##   O H    OCH.sub.3                                                                         O                                      H       H  H                                                                                 ##STR157##   O H    OCH.sub.3                                                                         O                                      H       H  H                                                                                 ##STR158##   O H    OCH.sub.3                                                                         O                                      H       H  H                                                                                 ##STR159##   O H    OCH.sub.3                                                                         O                                      H       H  H                                                                                 ##STR160##   O H    CH.sub.3                                                                          O                                      H       H  H                                                                                 ##STR161##   O H    Cl  O                                      H       H  H                                                                                 ##STR162##   O H    Cl  O                                      H       H  H                                                                                 ##STR163##   O H    OCH.sub.3                                                                         O                                      5-OC.sub.2 H.sub.5                                                                    H  H  CH.sub.3      O H    OCH.sub.3                                                                         O                                       ##STR164##                                                                           H  H  CH.sub.3      O H    OCH.sub.3                                                                         O                                      5-CF.sub.3                                                                            H  H                                                                                 ##STR165##   O H    OCH.sub.3                                                                         O                                      __________________________________________________________________________

                                      TABLE IXa                                   __________________________________________________________________________     ##STR166##                                                                   R      R.sub.1                                                                          R.sub.2                                                                          R.sub.12     W R.sub.8                                                                           Y'  m.p. (°C.)                         __________________________________________________________________________    H      H  H  H            O H   CH.sub.3                                      H      H  H  H            O H   OCH.sub.3                                     H      H  H  CH.sub.3     O H   CH.sub.3                                      H      H  H  CH.sub.3     O H   OCH.sub.3                                     H      H  H  CH.sub.2 CH.sub.3                                                                          O H   CH.sub.3                                      H      H  H  CH(CH.sub.3).sub.2                                                                         O H   CH.sub.3                                      H      H  H  CH(CH.sub.3).sub.2                                                                         O H   OCH.sub.3                                     H      H  H                                                                                 ##STR167##  O H   OCH.sub.3                                     H      H  H  CH.sub.2 CHCH.sub. 2                                                                       O H   OCH.sub.3                                     H      H  H                                                                                 ##STR168##  O H   CH.sub.3                                      H      H  H                                                                                 ##STR169##  O H   OCH.sub.3                                     H      H  H                                                                                 ##STR170##  O H   OCH.sub.3                                     H      H  CH.sub.3                                                                         CH.sub.3     O H   OCH.sub.3                                     H      CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3     O H   OCH.sub.3                                     3-F    H  H  CH.sub.3     O H   OCH.sub.3                                     5-Cl   H  H  CH.sub.3     O H   OCH.sub.3                                     5-CH.sub.3                                                                           H  H  CH.sub.3     O H   OCH.sub.3                                     5-NO.sub.2                                                                           H  H  CH.sub.3     O H   OCH.sub.3                                     4-OCH.sub.3                                                                          H  H  CH.sub.3     O H   OCH.sub.3                                     5-CF.sub.3                                                                           H  H  CH.sub.3     O H   OCH.sub.3                                     5-Cl   H  H  CH.sub.3     O H   CH.sub.3                                      6-Cl   H  H  CH.sub.3     O H   CH.sub.3                                      H      H  H  CH.sub.3     O H   H                                             H      H  H  CH.sub.3     O H   H                                             H      H  H  CH.sub.3     O H   Cl                                            H      H  H  CH.sub.3     O H   CH.sub.3                                      H      H  H  CH.sub.3     O H   OCH.sub.3                                     H      H  H  CH.sub.3     S H   CH.sub.3                                      H      H  H  CH.sub.3     S H   OCH.sub.3                                     H      H  H  CH.sub.3     S H   CH.sub.3                                      H      H  H  CH.sub.3     S H   OCH.sub.3                                     H      H  H  CH.sub.3     O CH.sub.3                                                                          CH.sub.3                                      H      H  H  CH.sub.3     O CH.sub.3                                                                          CH.sub.3                                      H      H  H  CH.sub.3     O CH.sub.3                                                                          OCH.sub.3                                     H      H  H  CH.sub.3     O CH.sub.3                                                                          OCH.sub.3                                     H      H  H  CH.sub.3     O OCH.sub.3                                                                         CH.sub.3                                      H      H  H  CH.sub.3     O OCH.sub.3                                                                         CH.sub.3                                      H      H  H  CH.sub.3     O OCH.sub.3                                                                         OCH.sub.3                                     H      H  H  CH.sub.3     O OCH.sub.3                                                                         OCH.sub.3                                     H      H  H  CH.sub.3     O H   OC.sub.2 H.sub.5                              H      H  H  CH.sub.3     O H   OC.sub.2 H.sub.5                              H      H  H  CH.sub.2(CH.sub.2).sub.4 CH.sub.3                                                          O H   OCH.sub.3                                     H      H  H  CH.sub.2CHCHCH.sub.3                                                                       O H   CH.sub.3                                      H      H  H                                                                                 ##STR171##  O H   OCH.sub.3                                     H      H  H                                                                                 ##STR172##  O H   OCH.sub.3                                     H      H  H                                                                                 ##STR173##  O H   OCH.sub.3                                     H      H  H                                                                                 ##STR174##  O H   OCH.sub.3                                     H      H  H                                                                                 ##STR175##  O H   OCH.sub.3                                     H      H  H                                                                                 ##STR176##  O H   CH.sub.3                                      H      H  H                                                                                 ##STR177##  O H   Cl                                            H      H  H                                                                                 ##STR178##  O H   Cl                                            H      H  H                                                                                 ##STR179##  O H   OCH.sub.3                                     5-OC.sub.2 H.sub.5                                                                   H  H  CH.sub.3     O H   OCH.sub.3                                      ##STR180##                                                                          H  H  CH.sub.3     O H   OCH.sub.3                                     5-CF.sub.3                                                                           H  H                                                                                 ##STR181##  O H   OCH.sub.3                                     __________________________________________________________________________

                                      TABLE X                                     __________________________________________________________________________     ##STR182##                                                                   R       R.sub.1                                                                          R.sub.2                                                                          R.sub.13 W  R.sub.8                                                                          X       Y   m.p. (°C.)                    __________________________________________________________________________    H       H  H  CH.sub.3 O H   CH.sub.3                                                                              CH.sub.3                                 H       H  H  CH.sub.3 O H   CH.sub.3                                                                              OCH.sub.3                                H       H  H  CH.sub.3 O H   OCH.sub.3                                                                             OCH.sub.3                                H       H  H  CH.sub.2 CH.sub.3                                                                      O H   CH.sub.3                                                                              OCH.sub.3                                H       H  H  CH.sub.2 CH.sub.3                                                                      O H   OCH.sub.3                                                                             OCH.sub.3                                H       H  H                                                                                 ##STR183##                                                                            O H   CH.sub.3                                                                              OCH.sub.3                                H       H  H                                                                                 ##STR184##                                                                            O H   OCH.sub. 3                                                                            OCH.sub.3                                H       H  H                                                                                 ##STR185##                                                                            O H   CH.sub.3                                                                              OCH.sub.3                                H       H  H                                                                                 ##STR186##                                                                            O H   OCH.sub.3                                                                             OCH.sub.3                                H       H  CH.sub.3                                                                         CH.sub.3 O H   OCH.sub.3                                                                             OCH.sub.3                                H       CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3 O H   OCH.sub.3                                                                             OCH.sub.3                                5-F     H  H  CH.sub.3 O H   OCH.sub.3                                                                             OCH.sub.3                                5-Cl    H  H  CH.sub.3 O H   OCH.sub.3                                                                             OCH.sub.3                                5-CH.sub.3                                                                            H  H  CH.sub.3 O H   OCH.sub.3                                                                             OCH.sub.3                                3-NO.sub.2                                                                            H  H  CH.sub.3 O H   OCH.sub.3                                                                             OCH.sub.3                                5-OCH.sub.3                                                                           H  H  CH.sub.3 O H   OCH.sub.3                                                                             OCH.sub.3                                5-CF.sub.3                                                                            H  H  CH.sub.3 O H   OCH.sub.3                                                                             OCH.sub.3                                5-Cl    H  H  CH.sub.3 O H   CH.sub.3                                                                              OCH.sub.3                                6-Cl    H  H  CH.sub.3 O H   CH.sub.3                                                                              OCH.sub.3                                H       H  H  CH.sub.3 O H   Cl      Cl                                       H       H  H  CH.sub.3 O H   Cl      OCH.sub.3                                H       H  H  CH.sub.3 O H   Br      OCH.sub.3                                H       H  H  CH.sub.3 O H   CH.sub.2 CH.sub.3                                                                     OCH.sub.3                                H       H  H  CH.sub.3 O H   OCH.sub.2 CH.sub.3                                                                    CH.sub.3                                 H       H  H  CH.sub.3 O H   OCH(CH.sub. 3).sub.2                                                                  CH.sub.3                                 H       H  H  CH.sub.3 O H   CF.sub.3                                                                              OCH.sub.3                                H       H  H  CH.sub.3 O H   SCH.sub.3                                                                             OCH.sub.3                                H       H  H  CH.sub.3 O H   CH.sub.2 OCH.sub.3                                                                    CH.sub.3                                 H       H  H  CH.sub.3 O H   CH.sub.2 OCH.sub.3                                                                    OCH.sub.3                                H       H  H  CH.sub.3 O H   H       CH.sub.3                                 H       H  H  CH.sub.3 O H   H       OCH.sub.3                                H       H  H                                                                                 ##STR187##                                                                            O H   Cl      Cl                                       H       H  H                                                                                 ##STR188##                                                                            O H   OCH.sub.3                                                                             OCH.sub.3                                4-CH.sub.3                                                                            H  H  CH.sub.3 O H   OCH.sub.3                                                                             OCH.sub.3                                5-OC.sub.2 H.sub.5                                                                    H  H  CH.sub.3 O H   OCH.sub.3                                                                             OCH.sub.3                                 ##STR189##                                                                           H  H  CH.sub.3 O H   OCH.sub.3                                                                             OCH.sub.3                                H       H  H  CH.sub.2 (CH.sub.2).sub.4 CH.sub.3                                                     O H   OCH.sub.3                                                                             OCH.sub.3                                H       H  H  CH.sub.2 CH.sub.2 CH.sub.3                                                             O H   OCH.sub.3                                                                             OCH.sub.3                                4-CF.sub.3                                                                            H  H  CH.sub.3 O H   OCH.sub.3                                                                             OCH.sub.3                                H       H  H  CH.sub.3 O H   Cl      OCH.sub.3                                6-C.sub.2 H.sub.5                                                                     H  H  CH.sub.3 O H   Cl      Cl                                       H       H  H                                                                                 ##STR190##                                                                            O H   OCH.sub.3                                                                             OCH.sub.3                                H       H  H  CH.sub.3 S H   CH.sub.3                                                                              CH.sub.3                                 H       H  H  CH.sub. 3                                                                              S H   CH.sub.3                                                                              OCH.sub.3                                H       H  H  CH.sub.3 S H   OCH.sub.3                                                                             OCH.sub.3                                H       H  H  CH.sub.3 S CH.sub.3                                                                          CH.sub.3                                                                              CH.sub.3                                 H       H  H  CH.sub.3 S CH.sub.3                                                                          CH.sub.3                                                                              OCH.sub.3                                H       H  H  CH.sub.3 S CH.sub.3                                                                          OCH.sub.3                                                                             OCH.sub.3                                H       H  H  CH.sub.3 S OCH.sub.3                                                                         CH.sub.3                                                                              CH.sub.3                                 H       H  H  CH.sub.3 S OCH.sub.3                                                                         CH.sub.3                                                                              OCH.sub.3                                H       H  H  CH.sub.3 S OCH.sub.3                                                                         OCH.sub.3                                                                             OCH.sub.3                                __________________________________________________________________________

                                      TABLE XI                                    __________________________________________________________________________     ##STR191##                                                                   R       R.sub.1                                                                          R.sub.2                                                                          R.sub.13 W  R.sub.8                                                                          X       Y   Z         m.p.                       __________________________________________________________________________                                                       (°C.)               H       H  H  CH.sub.3 O H   CH.sub.3                                                                              CH.sub.3                                                                          CH                                   H       H  H  CH.sub.3 O H   CH.sub.3                                                                              OCH.sub.3                                                                         CH                                   H       H  H  CH.sub.3 O H   OCH.sub.3                                                                             OCH.sub.3                                                                         CH                                   H       H  H  CH.sub.2 CH.sub.3                                                                      O H   CH.sub.3                                                                              OCH.sub.3                                                                         CH                                   H       H  H  CH.sub.2 CH.sub.3                                                                      O H   OCH.sub.3                                                                             OCH.sub.3                                                                         CH                                   H       H  H                                                                                 ##STR192##                                                                            O H   CH.sub.3                                                                              CH.sub.3                                                                          CH                                   H       H  H                                                                                 ##STR193##                                                                            O H   CH.sub.3                                                                              OCH.sub.3                                                                         CH                                   H       H  H                                                                                 ##STR194##                                                                            O H   OCH.sub.3                                                                             OCH.sub.3                                                                         CH                                   H       H  H                                                                                 ##STR195##                                                                            O H   CH.sub.3                                                                              OCH.sub.3                                                                         CH                                   H       H  H                                                                                 ##STR196##                                                                            O H   OCH.sub.3                                                                             OCH.sub.3                                                                         CH                                   H       H  CH.sub.3                                                                         CH.sub.3 O H   OCH.sub.3                                                                             OCH.sub.3                                                                         CH                                   H       CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3 O H   OCH.sub.3                                                                             OCH.sub.3                                                                         CH                                   5-F     H  H  CH.sub.3 O H   OCH.sub.3                                                                             OCH.sub.3                                                                         CH                                   4-Cl    H  H  CH.sub.3 O H   OCH.sub.3                                                                             OCH.sub.3                                                                         CH                                   5-CH.sub.3                                                                            H  H  CH.sub.3 O H   OCH.sub.3                                                                             OCH.sub.3                                                                         CH                                   5-NO.sub.2                                                                            H  H  CH.sub.3 O H   OCH.sub.3                                                                             OCH.sub.3                                                                         CH                                   5-OCH.sub.3                                                                           H  H  CH.sub.3 O H   OCH.sub.3                                                                             OCH.sub.3                                                                         CH                                   5-CF.sub.3                                                                            H  H  CH.sub.3 O H   OCH.sub.3                                                                             OCH.sub.3                                                                         CH                                   5-Cl    H  H  CH.sub.3 O H   CH.sub.3                                                                              OCH.sub.3                                                                         CH                                   6-Cl    H  H  CH.sub.3 O H   CH.sub.3                                                                              OCH.sub.3                                                                         CH                                   H       H  H  CH.sub.3 O H   Cl      Cl  CH                                   H       H  H  CH.sub.3 O H   Cl      OCH.sub.3                                                                         CH                                   H       H  H  CH.sub.3 O H   Br      OCH.sub.3                                                                         CH                                   H       H  H  CH.sub.3 O H   CH.sub.2 CH.sub.3                                                                     OCH.sub.3                                                                         CH                                   H       H  H  CH.sub.3 O H   OCH.sub.2 CH.sub.3                                                                    CH.sub.3                                                                          CH                                   H       H  H  CH.sub.3 O H   OCH(CH.sub.3).sub.2                                                                   CH.sub.3                                                                          CH                                   H       H  H  CH.sub.3 O H   CF.sub.3                                                                              OCH.sub.3                                                                         CH                                   H       H  H  CH.sub.3 O H   SCH.sub.3                                                                             OCH.sub.3                                                                         CH                                   H       H  H  CH.sub.3 O H   CH.sub.2 OCH.sub.3                                                                    CH.sub.3                                                                          CH                                   H       H  H  CH.sub.3 O H   CH.sub.2 OCH.sub.3                                                                    OCH.sub.3                                                                         CH                                   H       H  H  CH.sub.3 O H   H       CH.sub.3                                                                          CH                                   H       H  H  CH.sub.3 O H   H       OCH.sub.3                                                                         CH                                   H       H  H                                                                                 ##STR197##                                                                            O H   Cl      Cl  CH                                   H       H  H                                                                                 ##STR198##                                                                            O H   OCH.sub.3                                                                             OCH.sub.3                                                                         CH                                   H       H  H  CH.sub.3 O H   H       CH.sub.3                                                                          CCl                                  H       H  H  CH.sub.3 O H   CH.sub.3                                                                              CH.sub.3                                                                          CCN                                  H       H  H  CH.sub.3 O H   CH.sub.3                                                                              CH.sub.3                                                                          CCH.sub.3                            H       H  H  CH.sub.3 O H   H       CH.sub.3                                                                          CCH.sub.3                            H       H  H  CH.sub.3 O H   CH.sub.3                                                                              CH.sub.3                                                                          CCH.sub.2 CH.sub.3                   H       H  H  CH.sub.3 O H   H       CH.sub.3                                                                          CCH.sub.2 CH.sub.3                   H       H  H  CH.sub.3 O H   Cl      Cl  CCH.sub.2 CH.sub.2 Cl                H       H  H  CH.sub.3 O H   H       CH.sub.3                                                                          CCH.sub.2 CH.sub.2 Cl                H       H  H  CH.sub.3 O H   CH.sub.3                                                                              CH.sub.3                                                                          CCH.sub.2 CH.sub.2 Cl                H       H  H  CH.sub.3 O H   CH.sub.3                                                                              CH.sub.3                                                                          CCH.sub.2 CHCH.sub.2                 H       H  H  CH.sub.3 O H   H       CH.sub.3                                                                          CCH.sub.2 CHCH.sub.2                 5-OC.sub.2 H.sub.5                                                                    H  H  CH.sub.3 O H   OCH.sub.3                                                                             OCH.sub.3                                                                         CH                                    ##STR199##                                                                           H  H  CH.sub.3 O H   OCH.sub.3                                                                             OCH.sub.3                                                                         CH                                   4-CF.sub.3                                                                            H  H  CH.sub.3 O H   OCH.sub.3                                                                             OCH.sub.3                                                                         CH                                   H       H  H  CH.sub.2 (CH.sub. 2).sub.4 CH.sub.3                                                    O H   OCH.sub.3                                                                             OCH.sub.3                                                                         CH                                   H       H  H  CH.sub.2 CH.sub.2 CH.sub.3                                                             O H   OCH.sub.3                                                                             CH.sub.3                                                                          CH                                   H       H  H  CH.sub.3 O H   Cl      Cl  CH                                   6-C.sub.2 H.sub.5                                                                     H  H  CH.sub.3 O H   Cl      Cl  CH                                   H       H  H                                                                                 ##STR200##                                                                            O H   OCH.sub.3                                                                             OCH.sub.3                                                                         CH                                   H       H  H  CH.sub.3 S H   CH.sub.3                                                                              CH.sub.3                                                                          CH                                   H       H  H  CH.sub.3 S H   CH.sub.3                                                                              OCH.sub.3                                                                         CH                                   H       H  H  CH.sub.3 S H   OCH.sub.3                                                                             OCH.sub.3                                                                         CH                                   H       H  H  CH.sub.3 O CH.sub.3                                                                          CH.sub.3                                                                              CH.sub.3                                                                          CH                                   H       H  H  CH.sub.3 O CH.sub.3                                                                          CH.sub.3                                                                              OCH.sub.3                                                                         CH                                   H       H  H  CH.sub.3 O CH.sub.3                                                                          OCH.sub.3                                                                             OCH.sub.3                                                                         CH                                   H       H  H  CH.sub.3 O OCH.sub.3                                                                         CH.sub.3                                                                              CH.sub.3                                                                          CH                                   H       H  H  CH.sub.3 O OCH.sub.3                                                                         CH.sub.3                                                                              OCH.sub.3                                                                         CH                                   H       H  H  CH.sub.3 O OCH.sub.3                                                                         OCH.sub.3                                                                             OCH.sub.3                                                                         CH                                   __________________________________________________________________________

                                      TABLE XII                                   __________________________________________________________________________     ##STR201##                                                                   R       R.sub.1                                                                          R.sub.2                                                                          R.sub.13                                                                              W R.sub.8                                                                           Y'  Q  m.p. (°C.)                          __________________________________________________________________________    H       H  H  CH.sub.3                                                                              O H   CH.sub.3                                                                          O                                             H       H  H  CH.sub.3                                                                              O H   OCH.sub.3                                                                         O                                             H       H  H  CH.sub.2 CH.sub.3                                                                     O H   CH.sub.3                                                                          O                                             H       H  H                                                                                 ##STR202##                                                                           O H   CH.sub.3                                                                          O                                             H       H  H                                                                                 ##STR203##                                                                           O H   OCH.sub.3                                                                         O                                             H       H  H                                                                                 ##STR204##                                                                           O H   OCH.sub.3                                                                         O                                             H       H  CH.sub.3                                                                         CH.sub. 3                                                                             O H   OCH.sub.3                                                                         O                                             H       CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                              O H   OCH.sub.3                                                                         O                                             5-F     H  H  CH.sub.3                                                                              O H   OCH.sub.3                                                                         O                                             5-Cl    H  H  CH.sub.3                                                                              O H   OCH.sub.3                                                                         O                                             3-CH.sub.3                                                                            H  H  CH.sub.3                                                                              O H   OCH.sub.3                                                                         O                                             5-NO.sub.2                                                                            H  H  CH.sub.3                                                                              O H   OCH.sub.3                                                                         O                                             5-OCH.sub.3                                                                           H  H  CH.sub.3                                                                              O H   OCH.sub.3                                                                         O                                             4-CF.sub.3                                                                            H  H  CH.sub.3                                                                              O H   OCH.sub.3                                                                         O                                             5-Cl    H  H  CH.sub.3                                                                              O H   CH.sub.3                                                                          O                                             6-Cl    H  H  CH.sub.3                                                                              O H   CH.sub.3                                                                          O                                             H       H  H  CH.sub.3                                                                              O H   H   O                                             H       H  H  CH.sub.3                                                                              O H   H   CH.sub.2                                      H       H  H  CH.sub.3                                                                              O H   Cl  CH.sub.2                                      H       H  H  CH.sub.3                                                                              O H   CH.sub.3                                                                          CH.sub.2                                      H       H  H  CH.sub.3                                                                              O H   OCH.sub.3                                                                         CH.sub.2                                      5-OC.sub.2 H.sub.5                                                                    H  H  CH.sub.3                                                                              O H   OCH.sub.3                                                                         O                                              ##STR205##                                                                           H  H  CH.sub.3                                                                              O H   OCH.sub.3                                                                         O                                             6-CH.sub.3                                                                            H  H  CH.sub.3                                                                              O H   OCH.sub.3                                                                         O                                             4-CF.sub.3                                                                            H  H  CH.sub. 3     OCH.sub.3                                                                         O                                             H       H  H  CH.sub.2 (CH.sub.2).sub.4 CH.sub.3                                                    O H   OCH.sub.3                                                                         O                                             H       H  H  CH.sub.2 CH.sub.2 CH.sub.3                                                            O H   OCH.sub.3                                                                         O                                             H       H  H                                                                                 ##STR206##                                                                           O H   OCH.sub.3                                                                         O                                             H       H  H                                                                                 ##STR207##                                                                           O H   CH.sub.3                                                                          O                                             H       H  H                                                                                 ##STR208##                                                                           O H   OCH.sub.3                                                                         O                                             H       H  H  CH.sub.3                                                                              S H   CH.sub.3                                                                          O                                             H       H  H  CH.sub.3                                                                              S H   OCH.sub.3                                                                         O                                             H       H  H  CH.sub.3                                                                              S H   CH.sub.3                                                                          CH.sub.2                                      H       H  H  CH.sub.3                                                                              S H   OCH.sub.3                                                                         CH.sub.2                                      H       H  H  CH.sub.3                                                                              O CH.sub.3                                                                          CH.sub.3                                                                          O                                             H       H  H  CH.sub.3                                                                              O CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.2                                      H       H  H  CH.sub.3                                                                              O CH.sub.3                                                                          OCH.sub.3                                                                         O                                             H       H  H  CH.sub.3                                                                              O CH.sub.3                                                                          OCH.sub.3                                                                         CH.sub.2                                      H       H  H  CH.sub.3                                                                              O OCH.sub.3                                                                         CH.sub.3                                                                          O                                             H       H  H  CH.sub.3                                                                              O OCH.sub.3                                                                         CH.sub.3                                                                          CH.sub.2                                      H       H  H  CH.sub.3                                                                              O OCH.sub.3                                                                         OCH.sub.3                                                                         O                                             H       H  H  CH.sub.3                                                                              O OCH.sub.3                                                                         OCH.sub.3                                                                         CH.sub.2                                      H       H  H  CH.sub.3                                                                              O H   OC.sub.2 H.sub.5                                                                  O                                             H       H  H  CH.sub.3                                                                              O H   OC.sub.2 H.sub.5                                                                  CH.sub.2                                      __________________________________________________________________________

                                      TABLE XIIa                                  __________________________________________________________________________     ##STR209##                                                                   R       R.sub.1                                                                          R.sub.2                                                                          R.sub.13                                                                              W R.sub.8                                                                           Y'  m.p. (°C.)                             __________________________________________________________________________    H       H  H  CH.sub.3                                                                              O H   CH.sub.3                                          H       H  H  CH.sub.3                                                                              O H   OCH.sub.3                                         H       H  H  CH.sub.2 CH.sub.3                                                                     O H   CH.sub.3                                          H       H  H                                                                                 ##STR210##                                                                           O H   CH.sub.3                                          H       H  H                                                                                 ##STR211##                                                                           O H   OCH.sub.3                                         H       H  H                                                                                 ##STR212##                                                                           O H   OCH.sub.3                                         H       H  CH.sub.3                                                                         CH.sub.3                                                                              O H   OCH.sub.3                                         H       CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                              O H   OCH.sub.3                                         5-F     H  H  CH.sub.3                                                                              O H   OCH.sub.3                                         5-Cl    H  H  CH.sub.3                                                                              O H   OCH.sub.3                                         3-CH.sub.3                                                                            H  H  CH.sub.3                                                                              O H   OCH.sub.3                                         5-NO.sub.2                                                                            H  H  CH.sub.3                                                                              O H   OCH.sub.3                                         5-OCH.sub.3                                                                           H  H  CH.sub.3                                                                              O H   OCH.sub.3                                         4-CF.sub.3                                                                            H  H  CH.sub.3                                                                              O H   OCH.sub.3                                         5-Cl    H  H  CH.sub.3                                                                              O H   CH.sub.3                                          6-Cl    H  H  CH.sub.3                                                                              O H   CH.sub.3                                          H       H  H  CH.sub.3                                                                              O H   H                                                 H       H  H  CH.sub.3                                                                              O H   H                                                 H       H  H  CH.sub.3                                                                              O H   Cl                                                H       H  H  CH.sub.3                                                                              O H   CH.sub.3                                          H       H  H  CH.sub.3                                                                              O H   OCH.sub.3                                         5-OC.sub.2 H.sub.5                                                                    H  H  CH.sub.3                                                                              O H   OCH.sub.3                                          ##STR213##                                                                           H  H  CH.sub.3                                                                              O H   OCH.sub.3                                         6-CH.sub.3                                                                            H  H  CH.sub.3                                                                              O H   OCH.sub.3                                         4-CF.sub.3                                                                            H  H  CH.sub.3      OCH.sub.3                                         H       H  H  CH.sub.2 (CH.sub.2).sub.4 CH.sub.3                                                    O H   OCH.sub.3                                         H       H  H  CH.sub.2 CH.sub.2 CH.sub.3                                                            O H   OCH.sub.3                                         H       H  H                                                                                 ##STR214##                                                                           O H   OCH.sub.3                                         H       H  H                                                                                 ##STR215##                                                                           O H   CH.sub.3                                          H       H  H                                                                                 ##STR216##                                                                           O H   OCH.sub.3                                         H       H  H  CH.sub.3                                                                              S H   CH.sub.3                                          H       H  H  CH.sub.3                                                                              S H   OCH.sub.3                                         H       H  H  CH.sub.3                                                                              S H   CH.sub.3                                          H       H  H  CH.sub.3                                                                              S H   OCH.sub.3                                         H       H  H  CH.sub.3                                                                              O CH.sub.3                                                                          CH.sub.3                                          H       H  H  CH.sub.3                                                                              O CH.sub.3                                                                          CH.sub.3                                          H       H  H  CH.sub.3                                                                              O CH.sub.3                                                                          OCH.sub.3                                         H       H  H  CH.sub.3                                                                              O CH.sub.3                                                                          OCH.sub.3                                         H       H  H  CH.sub.3                                                                              O OCH.sub.3                                                                         CH.sub.3                                          H       H  H  CH.sub.3                                                                              O OCH.sub.3                                                                         CH.sub.3                                          H       H  H  CH.sub.3                                                                              O OCH.sub.3                                                                         OCH.sub.3                                         H       H  H  CH.sub.3                                                                              O OCH.sub.3                                                                         OCH.sub.3                                         H       H  H  CH.sub.3                                                                              O H   OC.sub.2 H.sub.5                                  H       H  H  CH.sub.3                                                                              O H   OC.sub.2 H.sub.5                                  __________________________________________________________________________

Formulations

Useful formulations of the compounds of Formula I can be prepared inconventional ways. They include dusts, granules, pellets, solutions,suspensions, emulsions, wettable powders, emulsifiable concentrates andthe like. Many of these may be applied directly. Sprayable formulationscan be extended in suitable media and used at spray volumes of from afew liters to several hundred liters per hectare. High strengthcompositions are primarily used as intermediates for furtherformulation. The formulations, broadly, contain about 0.1% to 99% byweight of active ingredient(s) and at least one of (a) about 0.1% to 20%surfactant(s) and (b) about 1% to 99.9% solid or liquid diluent(s). Morespecifically, they will contain these ingredients in the followingapproximate proportions:

                  TABLE XIII                                                      ______________________________________                                                   Active*                                                                       Ingredient                                                                             Diluent (s)                                                                             Surfactant (s)                                  ______________________________________                                        Wettable Powders                                                                           20-90       0-74     1-10                                        Oil Suspensions,                                                              Emulsions, Solu-                                                              tions (including                                                              Emulsifiable                                                                  Concentrates  3-50      40-95     0-15                                        Aqueous Suspensions                                                                        10-50      40-84     1-20                                        Dusts         1-25      70-99     0-5                                         Granules and                                                                  Pellets      0.1-95       5-99.9  0-15                                        High Strength                                                                 Compositions 90-99       0-10     0-2                                         ______________________________________                                         *Active ingredient plus at least one of a surfactant or a diluent equals      100 weight percent.                                                      

Lower or higher levels of active ingredient can, of course, be presentdepending on the intended use and the physical properties of thecompound. Higher ratios of surfactant to active ingredient are sometimesdesirable, and are achieved by incorporation into the formulation or bytank mixing.

Typical solid diluents are described in Watkins, et al., "Handbook ofInsecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books,Caldwell, N.J. The more absorptive diluents are preferred for wettablepowders and the denser ones for dusts. Typical liquid diluents andsolvents are described in Marsden, "Solvents Guide", 2nd Ed.,Interscience, New York, 1950. Solubility under 0.1% is preferred forsuspension concentrates; solution concentrates are preferably stableagainst phase separation at 0° C. "McCutcheon's Detergents andEmulsifiers Annual", MC Publishing Corp., Ridgewood, N.J., as well asSisely and Wood, "Encyclopedia of Surface Active Agents", ChemicalPublishing Co., Inc., New York 1964, list surfactants and recommendeduses. All formulations can contain minor amounts of additives to reducefoam, caking, corrosion, microbiological growth, etc.

The methods of making such compositions are well known. Solutions areprepared by simply mixing the ingredients. Fine solid compositions aremade by blending and, usually, grinding as in a hammer or fluid energymill. Suspensions are prepared by wet milling (see, for example,Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made byspraying the active material upon preformed granular carriers or byagglomeration techniques. See J. E. Browning, "Agglomeration", ChemicalEngineering, Dec. 4, 1967, pp. 147ff and "Perry's Chemical Engineer'sHandbook", 5th Ed., McGraw-Hill, New York, 1973, pp. 8-57ff.

For further information regarding the art of formulation, see forexample:

H. M. Loux, U.S. Pat. No. 3,235,361, Feb. 15, 1966, Col. 6, line 16through Col. 7, line 19 and Examples 10 through 41.

R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, March 14, 1967, Col. 5, line43 through Col. 1, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58,132, 138-140, 162-164, 166, 167 and 169-182.

H. Gysin and E. Knusli, U.S. Pat. No. 2,891,855, June 23, 1959, Col. 5,line 66 through Col. 5, line 17 and Examples 1-4.

G. C. Klingman, "Weed Control as a Science", John Wiley & Sons, Inc.,New York, 1961, pp. 81-96.

J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., BlackwellScientific Publications, Oxford, 1968, pp. 101-103.

In the following examples, all parts are by weight unless otherwiseindicated.

EXAMPLE 8 Wettable Powder

    ______________________________________                                        N-[(4,6-Dimethoxypyrimidin-2-yl)amino-                                        carbonyl]-2-(hydroxymethyl)-                                                  benzenesulfonamide       80%                                                  sodium alkylnaphthalenesulfonate                                                                        2%                                                  sodium ligninsulfonate    2%                                                  synthetic amorphous silica                                                                              3%                                                  kaolinite                13%                                                  ______________________________________                                    

The ingredients are blended, hammer-milled until all the solids areessentially under 50 microns and then reblended and packaged.

EXAMPLE 9 Wettable Powder

    ______________________________________                                        N-[(4-6-Dimethoxy-1,3,5-triazin-2-yl)amino-                                   carbonyl]-2-(hydroxymethyl)-                                                  benzenesulfonamide       50%                                                  sodium alkylnaphthalenesulfonate                                                                        2%                                                  low viscosity methyl cellulose                                                                          2%                                                  diatomaceous earth       46%                                                  ______________________________________                                    

The ingredients are blended, coarsely hammer-milled and then air-milledto produce particles of essentially all below 10 microns in diameter.The product is reblended before packaging.

EXAMPLE 10 Granule

    ______________________________________                                        wettable powder of Example 9                                                                          5%                                                    attapulgite granules   95%                                                    (U.S.S. 20-40 mesh; 0.84-0.42 mm)                                             ______________________________________                                    

A slurry of wettable powder containing ≈25% solids is sprayed on thesurface of attapulgite granules in a double-cone blender. The granulesare dried and packaged.

EXAMPLE 11 Extruded Pellet

    ______________________________________                                        N-[(4,6-Dimethoxypyrimidin-2-yl)amino-                                        carbonyl]-2-(hydroxymethyl)-                                                  benzenesulfonamide       25%                                                  anhydrous sodium sulfate 10%                                                  crude calcium ligninsulfonate                                                                           5%                                                  sodium alkylnaphthalenesulfonate                                                                        1%                                                  calcium/magnesium bentonite                                                                            59%                                                  ______________________________________                                    

The ingredients are blended, hammer-milled and then moistened with about12% water. The mixture is extruded as cylinders about 3 mm diameterwhich are cut to produce pellets about 3 mm long. These may be useddirectly after drying, or the dried pellets may be crushed to pass aU.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S.No. 40 sieve (0.42 mm openings) may be packaged for use and the finesrecycled.

EXAMPLE 12 Oil Suspension

    ______________________________________                                        N-[(4,6-Dimethoxy-1,3,5-triazin-2-yl)amino-                                   carbonyl]-2-(hydroxymethyl)-                                                  benzenesulfonamide       25%                                                  polyoxyethylene sorbitol hexaoleate                                                                     5%                                                  highly aliphatic hydrocarbon oil                                                                       70%                                                  ______________________________________                                    

The ingredients are ground together in a sand mill until the solidparticles have been reduced to under about 5 microns. The resultingthick suspension may be applied directly, but preferably after beingextended with oils or emulsified in water.

EXAMPLE 13 Wettable Powder

    ______________________________________                                        N-[(4,5-Dimethoxypyrimidin-2-yl)amino-                                        carbonyl]-2-(hydroxymethyl)-                                                  benzenesulfonamide       20%                                                  sodium alkylnaphthalenesulfonate                                                                        4%                                                  sodium ligninsulfonate    4%                                                  low viscosity methyl cellulose                                                                          3%                                                  attapulgite              69%                                                  ______________________________________                                    

The ingredients are thoroughly blended. After grinding in a hammer-millto produce particles essentially all below 100 microns, the material isreblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) andpackaged.

EXAMPLE 14 Low Strength Granule

    ______________________________________                                        N-[(4,6-Dimethoxy-1,3,5-triazin-2-yl)-                                        aminocarbonyl]-2-(hydroxymethyl)-                                             benzenesulfonamide      1%                                                    N,N-dimethylformamide   9%                                                    attapulgite granules   90%                                                    (U.S.S. 20-40 sieve)                                                          ______________________________________                                    

The active ingredient is dissolved in the solvent and the solution issprayed upon dedusted granules in a double cone blender. After sprayingof the solution has been completed, the blender is allowed to run for ashort period and then the granules are packaged.

EXAMPLE 15 Aqueous Suspension

    ______________________________________                                        N-[(4,6-Dimethoxypyrimidin-2-yl)-                                             aminocarbonyl]-2-(hydroxymethyl)-                                             benzenesulfonamide        40%                                                 polyacrylic acid thickener                                                                              0.3%                                                dodecylphenol polyethylene glycol                                             ether                     0.5%                                                disodium phosphate        1%                                                  monosodium phosphate      0.5%                                                polyvinyl alcohol         1.0%                                                Water                     56.7%                                               ______________________________________                                    

The ingredients are blended and ground together in a sand mill toproduce particles essentially all under 5 microns in size.

EXAMPLE 16 Solution

    ______________________________________                                        N-[(4,6-Dimethoxypyrimidin-2-yl)-                                             aminocarbonyl]-2-(hydroxymethyl)-                                             benzenesulfonamide, sodium salt                                                                       5%                                                    water                  95%                                                    ______________________________________                                    

The salt is added directly to the water with stirring to produce thesolution, which may then be packaged for use.

EXAMPLE 17 Low Strength Granule

    ______________________________________                                        N-[(4,6-Dimethoxypyrimidin-2-yl)-                                             aminocarbonyl]-2-(hydroxymethyl)-                                             benzenesulfonamide     0.1%                                                   attapulgite granules  99.9%                                                   (U.S.S. 20-40 mesh)                                                           ______________________________________                                    

The active ingredient is dissolved in a solvent and the solution issprayed upon dedusted granules in a double cone blender. After sprayingof the solution has been completed, the material is warmed to evaporatethe solvent. The material is allowed to cool and then packaged.

EXAMPLE 18 Granule

    ______________________________________                                        N-[(4,6-Dimethoxy-1,3,5-triazin-2-yl)-                                        aminocarbonyl]-2-(hydroxymethyl)-                                             benzenesulfonamide     80%                                                    wetting agent           1%                                                    crude ligninsulfonate salt (containing                                        5-20% of the natural sugars)                                                                         10%                                                    attapulgite clay        9%                                                    ______________________________________                                    

The ingredients are blended and milled to pass through a 100 meshscreen. This material is then added to a fluid bed granulator, the airflow is adjusted to gently fluidize the material, and a fine spray ofwater is sprayed onto the fluidized material. The fluidization andspraying are continued until granules of the desired size range aremade. The spraying is stopped, but fluidization is continued, optionallywith heat, until the water constant is reduced to the desired level,generally less than 1%. The material is then discharged, screened to thedesired size range, generally 14-100 mesh (1410-149 microns), andpackaged for use.

EXAMPLE 19 High Strength Concentrate

    ______________________________________                                        N-[(4,6-Dimethoxypyrimidin-2-yl)-                                             aminocarbonyl]-2-(hydroxymethyl)-                                             benzenesulfonamide      99%                                                   silica aerogel         0.5%                                                   synthetic amorphous silica                                                                           0.5%                                                   ______________________________________                                    

The ingredients are blended and ground in a hammer-mill to produce amaterial essentially all passing a U.S.S. No. 50 screen (0.3 mmopening). The concentrate may be formulated further if necessary.

EXAMPLE 20 Wettable Powder

    ______________________________________                                        N-[(4,6-Dimethoxy-1,3,5-triazin-2-yl)-                                        aminocarbonyl]-2-(hydroxymethyl)-                                             benzenesulfonamide      90%                                                   dioctyl sodium sulfosuccinate                                                                        0.1%                                                   synthetic fine silica  9.9%                                                   ______________________________________                                    

The ingredients are blended and ground in a hammer-mill to produceparticles essentially all below 100 microns. The material is siftedthrough a U.S.S. No. 50 screen and then packaged.

EXAMPLE 21 Wettable Powder

    ______________________________________                                        N-[(4,6-Dimethoxy-1,3,5-triazin-2-yl)-                                        aminocarbonyl]-2-(hydroxymethyl)-                                             benzenesulfonamide     40%                                                    sodium ligninsulfonate 20%                                                    montmorillonite clay   40%                                                    ______________________________________                                    

The ingredients are thoroughly blended, coarsely hammer-milled and thenair-milled to produce particles essentially all below 10 microns insize. The material is reblended and then packaged.

EXAMPLE 22 Oil Suspension

    ______________________________________                                        N-[(4,6-Dimethoxy-1,3,5-triazin-2-yl)-                                        aminocarbonyl]-2-(hydroxymethyl)-                                             benzenesulfonamide     35%                                                    blend of polyalcohol carboxylic                                               esters and oil soluble petroleum                                              sulfonates              6%                                                    xylene                 59%                                                    ______________________________________                                    

The ingredients are combined and ground together in a sand mill toproduce particles essentially all below 5 microns. The product can beused directly, extended with oils, or emulsified in water.

Utility

The compounds of the present invention are active herbicides. They haveutility for broadspectrum pre- and/or post-emergence weed control inareas where complete control of all vegetation is desired, such asaround fuel storage tanks, ammunition depots, industrial storage, areas,oil well sites, drive-in theaters, around billboards, highway andrailroad structures. By properly selecting rate and time of application,compounds of this invention may be used to modify plant growthbeneficially, and also selectively control weeds in crops such as wheat.

The precise amount of the compound of Formula I to be used in any givensituation will vary according to the particular end result desired, theamount of foliage present, the weeds to be controlled, the soil type,the formulation and mode of application, weather conditions, etc. Sinceso many variables play a role, it is not possible to state a rate ofapplication suitable for all situations. Broadly speaking, the compoundsof this invention are used at levels of about 0.05 to 20 kg/ha with apreferred range of 0.1 to 10 kg/ha. In general, the higher rates ofapplication from within this range will be selected for adverseconditions or where extended persistence in soil is desired.

The compounds of Formula I may be combined with other herbicides and areparticularly useful in combination with3-(3,4-dichlorophenyl)-1,1-dimethylurea (diuron); the triazines such as2-chloro-4-(ethylamino)-6-(isopropylamino)-s-triazine (atrazine); theuracils such as 5-bromo-3-sec-butyl-6-methyluracil (bromacil);N-(phosponomethyl)glycine (glyphosate);3-cyclohexyl-1-methyl-6-dimethylamino-s-triazine-2,4(1H,3H)-dione(hexazinone); N,N-dimethyl-2,2-diphenylacetamide (diphenamide);2,4-dichlorophenoxyacetic acid (2,4-d) (and closely related compounds);4-chloro-2-butynyl-3-chlorophenylcarbamate (barban);S-(2,3-dichloroallyl)diisopropylthiocarbamate (diallate);S-(2,3,3-trichloroallyl)diisopropylthiocarbamate (triallate);1,2-dimethyl-3,5-diphenyl-1H-pyrazolium methyl sulfate (difenzoquatmethyl sulfate); methyl 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoate(diclofop methyl);4-amino-6-tert-butyl-3-(methylthio)-1,2,4-triazin-5(4H)one (metribuzin);3-(3,4-dichlorophenyl)-1-methoxy-1-methylurea (linuron);3-isopropyl-1H-2,1,3-benzothiodiazin-4(3H)-one-2,2-dioxide (bentazon);α,α,α-trifluoro-2,6-dinitro-N,N-dipropyl-p-toluidine (trifluralin);1,1'-dimethyl-4,4'-bipyridinium ion (paraquat);2-chloro-2',6'-diethyl(methoxymethyl)acetanilide (alachlor);1,1-dimethyl-3-(α,α,α-trifluoro-m-tolyl)urea (fluometuron);S-(4-chlorobenzyl)N,N-diethylthiolcarbamate (benthiocarb);N-(butoxymethyl)-2-chloro-2',6'-diethylacetanilide (butachlor); and5-[2-chloro-5-(trifluoromethyl)phenoxy]-2-nitrobenzoic acid, methylester (acifluorfen-methyl).

Test Procedure A

Seeds of crabgrass (Digitaria spp.), barnyardgrass (Echinochloacrusgalli), wild oats (Avena fatua), cassia (Cassia tora), morningglory(Ipomoea spp.), cocklebur (Xanthium spp.), sorghum, corn, soybean, rice,wheat and nutsedge tubers (Cyperus rotundus) were planted in a growthmedium and treated preemergence with the chemicals dissolved in anonphytotoxic solvent. At the same time, cotton having five leaves(including cotyledonary ones), bush beans with the third trifoliolateleaf expanding, crabgrass with two leaves, barnyardgrass with twoleaves, wild oats with one leaf, cassia with three leaves (includingcotyledonary ones), morningglory with four leaves (including thecotyledonary ones), cocklebur with four leaves (including thecotyledonary ones), sorghum with three leaves, corn with three leaves,soybean with two cotyledonary leaves, rice with two leaves, wheat withone leaf, and nutsedge with three to five leaves were sprayed. Treatedplants and controls were maintained in a greenhouse for 16 days, thenall species were compared to controls and visually rated for response totreatment.

Ratings for compounds tested by this procedure are recorded in TableXIV.

0=no effect

10=maximum effect

C=chlorosis or necrosis

D=defoliation

E=emergence inhibition

G=growth retardation

H=formative effects

6Y=abscised buds or flowers.

                  TABLE XIV                                                       ______________________________________                                                    ##STR217##                                                        ______________________________________                                        kg/ha        0.05                                                             POST-EMERGENCE                                                                BUSH BEAN    5C, 10D, 6Y                                                      COTTON       3C, 4H, 8G                                                       MORNINGGLORY 2G                                                               COCKLEBUR    5C, 9G                                                           CASSIA       5C, 9G                                                           NUTSEDGE     1C, 9G                                                           CRABGRASS    3G                                                               BARNYARDGRASS                                                                              3C, 9H                                                           WILD OATS    1C, 3G                                                           WHEAT        0                                                                CORN         2C, 9H                                                           SOYBEAN      9C                                                               RICE         2C, 9G                                                           SORGHUM      2C, 9H                                                           PRE-EMERGENCE                                                                 MORNINGGLORY 8G                                                               COCKLEBUR    9H                                                               CASSIA       1C, 8G                                                           NUTSEDGE     10E                                                              CRABGRASS    2C                                                               BARNYARDGRASS                                                                              2C, 9H                                                           WILD OATS    8G, O                                                            WHEAT        6G, O                                                            CORN         1C, 9H                                                           SOYBEAN      2C, 8H                                                           RICE         10E                                                              SORGHUM      2C, 9G                                                           ______________________________________                                    

                  TABLE XV                                                        ______________________________________                                                    ##STR218##                                                        ______________________________________                                        kg/ha        0.05                                                             POST-EMERGENCE                                                                BUSHBEAN     2C, 7G, 6Y                                                       COTTON       0                                                                MORNINGGLORY 1C                                                               COCKLEBUR    0                                                                CASSIA       1C                                                               NUTSEDGE     0                                                                CRABGRASS    2G                                                               BARNYARDGRASS                                                                              0                                                                WILD OATS    0                                                                WHEAT        0                                                                CORN         2C, 9H                                                           SOYBEAN      1C, 6H                                                           RICE         1C, 4G                                                           SORGHUM      2C, 9H                                                           PRE-EMERGENCE                                                                 MORNINGGLORY 2C                                                               COCKLEBUR    0                                                                CASSIA       1C                                                               NUTSEDGE     0                                                                CRABGRASS    0                                                                BARNYARDGRASS                                                                              2C, 7H                                                           WILD OATS    0                                                                WHEAT        0                                                                CORN         9H                                                               SOYBEAN      2C, 3H                                                           RICE         1C                                                               SORGHUM      2C, 9H                                                           ______________________________________                                    

What is claimed is:
 1. A compound selected from ##STR219## wherein L isOH, OC(O)R₁₁, OC(O)NHR₁₂ or OC(O)OR₁₃ ;R is H, F, Cl, Br, NO₂, CF₃, C₁-C₃ alkyl or C₁ -C₃ alkoxy; R₁ is H or C₁ -C₄ alkyl; R₂ is H or CH₃ ; R₈is H, CH₃ or OCH₃ ; R₁₁ is H, C₁ -C₅ alkyl, C₂ -C₃ alkenyl, C₂ -C₃alkynyl, C₃ -C₄ cycloalkyl, ##STR220## C₁ -C₄ alkyl substituted with 1-4substituents selected from 0-3 F, 0-3 Cl or 0-3 Br or C₂ -C₃ alkenylsubstituted with 1-3 Cl; R₁₂ is H, C₁ -C₆ alkyl, C₃ -C₄ alkenyl, C₅ -C₆cycloalkyl, ##STR221## C₅ -C₆ cycloalkyl substituted with CH₃ ; R₁₃ isC₁ -C₆ alkyl or ##STR222## R₁₄ and R₁₅ are independently H, NO₂, CH₃, Clor OCH₃ ; R₁₆ is H, F, Cl, Br, C₁ -C₃ alkyl, NO₂, CN, SO₂ CH₃, OCH₃,SCH₃ or CF₃ ; R₁₇ is H, Cl or C₁ -C₃ alkyl; R₁₈ is H, CH₃ or Cl; A is##STR223## W is O or S; X is H, Cl, Br, CH₃, CH₂ CH₃, C₁ -C₃ alkoxy,CF₃, SCH₃ or CH₂ OCH₃ ; Y is CH₃ or OCH₃ ; Z is N, CH, CCl, CBr, CCN,CCH₃, CCH₂ CH₃, CCH₂ CH₂ Cl or CCH₂ CH═CH₂ ; Y¹ is H, CH₃, OCH₃ or OCH₂CH₃ ; and Q is O or CH₂ ;and their agriculturally suitable salts;provided that when W is S, then R₈ is H.
 2. A compound of claim 1 whereZ is N, CH, CCl, CBr or CCH₃, W is O and R₈ is H or CH₃.
 3. A compoundof claim 1 where L is OH; R is H; R₁ and R₂ are CH₃ ; and R₈ is H or CH₃; A is ##STR224## Z is CH or N; X and Y are independently CH₃ or OCH₃ ;and W is O.
 4. A compound of claim 2 where Z is CH or N; X is CH₃ orOCH₃ ; and R₁ is H or CH₃.
 5. A compound of claim 4 where R and R₈ areH, and A is ##STR225##
 6. A compound of claim 5 where R₁₁, R₁₂ and R₁₃are C₁ -C₃ alkyl.
 7. A compound of claim 5 where L is OH.
 8. Thecompound of claim 1,N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(hydroxymethyl)benzenesulfonamide.9. The compound of claim 1,N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-(hydroxymethyl)benzenesulfonamide.10. The compound of claim 1,N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-(hydroxymethyl)benzenesulfonamide.11. The compound of claim 1,N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-(hydroxymethyl)benzenesulfonamide.12. The compound of claim 1,N-[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-(hydroxymethyl)benzenesulfonamide.13. The compound of claim 1,N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-(hydroxymethyl)benzenesulfonamide.14. A composition for the control of undesirable vegetation consistingessentially of a compound of claim 1 and at least one of (a) asurface-active agent and (b) a solid or liquid diluent.
 15. Acomposition for the control of undesirable vegetation consistingessentially of a compound of claim 2 and at least one of (a) asurface-active agent and (b) a solid or liquid diluent.
 16. Acomposition for the control of undesirable vegetation consistingessentially of a compound of claim 3 and at least one of (a) asurface-active agent and (b) a solid or liquid diluent.
 17. Acomposition for the control of undesirable vegetation consistingessentially of a compound of claim 4 and at least one of (a) asurface-active agent and (b) a solid or liquid diluent.
 18. Acomposition for the control of undesirable vegetation consistingessentially of a compound of claim 5 and at least one of (a) asurface-active agent and (b) a solid or liquid diluent.
 19. Acomposition for the control of undesirable vegetation consistingessentially of a compound of claim 6 and at least one of (a) asurface-active agent and (b) a solid or liquid diluent.
 20. A method forthe control of undesirable vegetation consisting of applying to thelocus of such undesirable vegetation a herbicidally effective amount ofa compound of claim
 1. 21. A method for the control of undesirablevegetation comprising applying to the locus of such undesirablevegetation a herbicidally effective amount of a compound of claim
 2. 22.A method for the control of undesirable vegetation comprising applyingto the locus of such undesirable vegetation a herbicidally effectiveamount of a compound of claim
 3. 23. A method for the control ofundesirable vegetation comprising applying to the locus of suchundesirable vegetation a herbicidally effective amount of a compound ofclaim
 4. 24. A method for the control of undesirable vegetationcomprising applying to the locus of such undesirable vegetation aherbicidally effective amount of the compound of claim
 5. 25. A methodfor the control of undesirable vegetation comprising applying to thelocus of such undesirable vegetation a herbicidally effective amount ofthe compound of claim 6.